DOCSLIB.ORG

Us 8614320 B2 Compounds 2931

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Us 8614320 B2 Compounds 2931 USOO8614320B2 (12) United States Patent (10) Patent No.: US 8,614,320 B2 Matsushita et al. (45) Date of Patent: *Dec. 24, 2013 (54) PREPARATION OF AMINOPYRIMIDINE 4,968,681. A 1 1/1990 Hubsch et al. COMPOUNDS 2931. A 3: WaySS a (75) Inventors: Akio Matsushita, Ube (JP); Mizuho 3.03. A E. E. et al. Oda, Yamaguchi (JP); Yasuhiro 5,260,440 A 1 1/1993 Hirai et al. Kawachi, Yamaguchi (JP); Jun-ichi 5,278,313 A 1/1994 Thottathil et al. Chika, Yamaguchi (JP) 3.-- I A E OlaReal ea. 5,681,957 A 10, 1997 Wolters et al. (73) Assignee: strences UK Limited, London 6,278,001 B1 8, 2001 Solladie et al. 6,331,641 B1 12/2001 Taoka et al. 6,579,984 B1 6/2003 Veith et al. (*) Notice: Subject to any disclaimer, the term of this 6,689,591 B2 2/2004 Muller et al. patent is extended or adjusted under 35 6,784, 171 B2 8/2004 Taylor et al. U.S.C. 154(b) by 0 days. (Continued) This patent is Subject to a terminal dis- FOREIGN PATENT DOCUMENTS claimer. EP O252476 1, 1988 (21) Appl. No.: 13/523,534 EP O319845 6, 1989 (22) Filed: Jun. 14, 2012 other instektions (65) Prior Publication Data Anne et al. "Enantioselective synthesss of key A-ring precursors of US 2012/O277432 A1 Nov. 1, 2012 lo, 25-dihydroxyvitamin D and analogues' Synlett 9:1435-1437 s (1999). O O Bhaskar Reddy et al. "Enantioselective synthesis of B-hydroxy Related U.S. Application Data Ö-lactones: a new approach to the synthetic congeners of 3-hydroxy (62) Division of application No. 12/889,186, filed on Sep. Insthylglutayneyme A reductase inhibitors" J. Org, Chem. 23,faroplication 2010, now No.Pat. 1No. 1/933,626, 8,222.412, filed which on Nov. is a division1, 2007 Blandin22(?). et al. "One-pot and sequential asymmetric hydrogenation of of application No. s Illed on Nov. 1, s B,6-diketoesters into functionalized 1,3-diols: From anti- to syn now Pat. No. 7,816,528, which is a division of stereoselectivity” European Journal of Organic Chemistry 12:3421 application No. 10/483,430, filed as application No. 3427 (1999). PCT/JP02/07129 on Jul 12, 2002, now Pat. No. Continued 7,304,156. (Continued) Primary Examiner — Venkataraman Balasubramanian (30) Foreign Application Priority Data (74) Attorney, Agent, or Firm — Morgan, Lewis & Bockius LLP Jul. 13, 2001 (JP) ................................. 2001-213417 Jul. 13, 2001 (JP) ................................. 2001-213418 (57) ABSTRACT - Oct. 9, 2001 (JP) ................................. 2001-310900 A 2-(N-methyl-N-methanesulfonylamino)pyrimidine com Nov. 27, 2001 (JP) ................................. 2001-360339 pound of the formula (3): R is a hydrocarbyl group), is Jan. 1 6. 2002 (JP) 2002-007O15 prepared by the steps of (I) reacting an isobutyrylacetate Feb. 1 9. 2002 (JP). 2002-042O76 ester with 4-fluorobenzaldehyde and urea in the presence of a • u. -- s 1- w 1 vs - F · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · protonic compound and a metal salt; (II) oxidizing the reac (51) Int. Cl t1Onoroduction product Ofof the Stestep (I); (III react1nging the OX1Cat1Onoroductoxidation produ cond 239/36 2006.O1 of the step (II) with an organic sulfonyl halide or an organic CO7D 239/42 (2OO 6. O sulfonyl anhydride; and (IV) reacting the reaction product of C07D 239/22 3:08: the step (III) with N-methyl-N-methanesulfonamide. A61 K3 1/505 (2006.01) A6IP3/06 (2006.01) (3) (52) U.S. Cl. F USPC ............................ 544/315:544/316:544/330 (58) Field of Classification Search USPC .......................................... 544/315, 316,330 See application file for complete search history. (56) References Cited COR U.S. PATENT DOCUMENTS O lN1N S 4,613,610 A 9/1986 Wareing HC1 YN 4. 4,625,039 A 1 1/1986 Jewell, Jr. et al. O 4,645,858 A 2f1987 Lowrie et al. 4,650,890 A 3/1987 Jewell, Jr. et al. 4,677,211 A 6/1987 Jewell, Jr. et al. 4,957,971 A 9, 1990 Picard et al. 4 Claims, No Drawings US 8,614,320 B2 Page 2 (56) References Cited WO WO 2005/042522 5, 2005 WO WO 2005/047 276 5, 2005 U.S. PATENT DOCUMENTS WO WO 2005/063728 7/2005 WO WO 2005/092867 10/2005 6,844,437 B1 1/2005 Taylor et al. WO WO 2006/067456 6, 2006 6,855,716 B2 2/2005 Ohno et al. WO WO 2006/0894O1 8, 2006 6,870,059 B2 3/2005 Kooistra et al. WO WO 2007/007119 1, 2007 7,157.255 B2 1/2007 Blacker et al. 7,199,140 B2 4/2007 Hayter et al. OTHER PUBLICATIONS 7,304,156 B2 12/2007 Matsushita et al. BouzBouzetal. “Regioselective Cross-Metathesis Reaction Induced 7,416,865 B2 8, 2008 Blacker et al. by Steric Hindrance” Organic Letters 6(20):3465-3467 (2004). 7,442,811 B2 10/2008 Bakel Van et al. Bovyet al. “Synthesis of Heterocyclic B-Amino Acids. A convenient 7,511,140 B2 3/2009 Horbury et al. preparation of 3-Amino-5-pyrimidinepropanoic acid and deriva 7,642,3637,524.955 B2 4/20091/2010 NewtonKooistra etet al. al. tives’ Tetrahedron& 8 Letters 34(50):8015-8018 (1993). 7,718,812 B2 5, 2010 Hof et al. Breaux et al. "An Improved General Synthesis of 4-Aryl-5- 7,732,171 B2 6, 2010 Blacker et al. Pyrimidinecarboxylates' J. Heterocyclic Chem. 18: 183 (1981). 7.816,528 B2 10/2010 Matsushita et al. Casini et al. “Carbonic anhydrase inhibitors with strong topical 7,842,807 B2 11/2010 Horbury et al. antiglaucoma properties incorporating a 4-(2-amino-pyrimidin-4-yl 7,888,083 B2 2/2011 Blacker et al. amino)-benzenesulfonamide scaffold” Journal of Enzyme Inhibition 7.989,643 B2 8/2011 Kooistra et al. and Medicinal Chemistry 17(1):9-18 (2002). 8,034,932 B2 10/2011 Butters et al. Castro et al. "A new synthesis of 3,5-dihydroxy-7-(1-pyrrolyl)-6- 8,063,213 B2 11/2011 Crabb et al. heptenoic acids, a family of HMGCoA reductase inhibitors with 2003, OO18199 A1 1/2003 Brodfuehrer et al. ----- 2005, 0124639 A1 6, 2005 Joshi et al. antifungal activity”& 8 Tetrahedron Letters 43:1851-1854 (2002). 2006, O293355 A1 12, 2006 Booth et al. De Luca et al. "Cellulose Beads: a New Versatile Solid Support for 2007/0093660 A1 4/2007 Tararov et al. Microwave-Assisted Synthesis. Preparation of Pyrazole and 2007/0105882 A1 5, 2007 Black et al. Isoxazole Libraries” J. Comb. Chem. 5(4):465-471 (2003). 2007,0255060 A1 11, 2007 Okada et al. Denmark et al. “The Chemistry of Trichlorosilyl Enolates. Aldol 2008. O188657 A1 8/2008 Lenger Addition Reactions of Methyl Ketones' J. Am. Chem. Soc. 122 2008/02O7903 A1 8, 2008 Butters et al. (37):8837-8847 (2000). 2008, 0221323 A1 9, 2008 Crabb et al. Dovlatyan et al. “Studies on functionally-substituted azines. 8. Syn 2009,0264654 A1 10, 2009 Newton et al. thesis and transformations of 1-arylsulfonylamido-4-methoxy-6- 2010/0222373 A1 9, 2010 Booth et al. methylpyrimidines' Chemistry of Heterocyclic Compounds 2010/0228028 A1 9, 2010 Butters et al. 36(11): 1306-1313(2000). 2012,005.9022 A1 3/2012 Booth et al. Evans et al. “Diastereoselective synthesis of protected syn 1,3-diols by base-catalyzed intramolecular conjugate addition of hemiacetal FOREIGN PATENT DOCUMENTS derived alkoxide nucleophiles' J. Org. Chem. 58:2446-2453 (1993). EP O3 19847 6, 1989 Feuerstein et al. "A new efficient tetraphosphine/palladium catalyst EP O742212 11, 1996 for the Heck reaction of arvlhalidesy with stvirenetyr or vinylethery deriva EP O521471 10, 2000 tives’ Tetrahedron Letters 43:2191-2194 (2002). EP 1193,259 4/2002 Grohe et al. “Synthese and Reaktionen von 2,4-Dichlorpyrimidin-5- GB 2244705 12/1991 carbon-Saureestem” Liebigs Ann. Chem. 1025-1035 (1973). JP 5-178841 7, 1993 Guetal. “Synthesis ofent-Haterumalide NA(ent-Oocydin A) Methyl JP 6-256318 9, 1994 Ester” Organic Letters 5(23):4385-4388 (2003). WO WO90,03973 4f1990 & 8 WO WO92fO1675 2, 1992 Hannah et al. “Structural studies on bioactive compounds. Part 29: WO WO93,08823 5, 1993 palladium catalysed arylations and alkynylations of sterically hin WO WO 96.14846 4f1996 dered immunomodulatory 2-amino-5-halo-4,6- WO WO 97/19917 6, 1997 (disubstituted)pyrimidines' Bioorg Med Chem. 8(4):739-750 WO WO 97.21687 6, 1997 (2000). WO WO99.07695 4f1999 Hauser et al. “Synthesis of 5-phenyl-4,6-dimethyl-2-pyrimidol and WO WOOOf 49014 8, 2000 WO WOOOf7873O 12/2000 derivatives from the cyclization of urea with 3-phenyl-2,4- WO WOO1/4100 1, 2001 pentanedione” Journal of Organic Chemistry 18(5): 588-593 (1953). WO WOO1,04336 1, 2001 Hiyama et al. “Synthesis of Artificial HMG-CoA Reductase Inhibi WO WOO1? 60804 8, 2001 tors Based on the Olefination Strategy” Bull. Chem. Soc. Jpn. 68 WO WOO1,727O6 10, 2001 (1):364-372 (1995). WO WOO1f85702 11, 2001 Kaneko et al. "Preparation of optically active 5,6-epoxyhexanoic WO WOO1/859.75 11, 2001 acid esters as materials for physiologically active Substances' WO WOO2,05519 1, 2002 WO WOO2,06266 1, 2002 Chemical Abstracts +Indexes, American Chemical Society, Colum WO WOO3,OO4450 1, 2003 bus, US 118(11):832 (1993). WO WOO3,OO6439 1, 2003 Littke et al. "A Versatile Catalyst for Heck Reactions of Aryl Chlo WO WOO3,O18555 3, 2003 rides and Aryl Bromides under Mild Conditions' J. Am. Chem. Soc. WO WOO3,059901 T 2003 123(29):6989-7000 (2001). WO WOO3,064382 8, 2003 Littke et al.
Load more

Recommended publications
  • Methanesulfonyl Chloride
    A Publication of Reliable Methods for the Preparation of Organic Compounds Working with Hazardous Chemicals The procedures in Organic Syntheses are intended for use only by persons with proper training in experimental organic chemistry. All hazardous materials should be handled using the standard procedures for work with chemicals described in references such as "Prudent Practices in the Laboratory" (The National Academies Press, Washington, D.C., 2011; the full text can be accessed free of charge at http://www.nap.edu/catalog.php?record_id=12654). All chemical waste should be disposed of in accordance with local regulations. For general guidelines for the management of chemical waste, see Chapter 8 of Prudent Practices. In some articles in Organic Syntheses, chemical-specific hazards are highlighted in red “Caution Notes” within a procedure. It is important to recognize that the absence of a caution note does not imply that no significant hazards are associated with the chemicals involved in that procedure. Prior to performing a reaction, a thorough risk assessment should be carried out that includes a review of the potential hazards associated with each chemical and experimental operation on the scale that is planned for the procedure. Guidelines for carrying out a risk assessment and for analyzing the hazards associated with chemicals can be found in Chapter 4 of Prudent Practices. The procedures described in Organic Syntheses are provided as published and are conducted at one's own risk. Organic Syntheses, Inc., its Editors, and its Board of Directors do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein.
    [Show full text]
  • 덴드리틱 벤질 클로라이드의 효율적인 합성 Facile Synthesis of Dendritic Benzyl Chlorides from Their Alcohols W
    Polymer(Korea), Vol. 31, No. 5, pp 417-421, 2007 덴드리틱 벤질 클로라이드의 효율적인 합성 이재욱F,7ㆍ한승철Fㆍ김희주ㆍ김정환ㆍ이언엽ㆍ김병기ㆍ성새름ㆍ강화신ㆍ김지현FFㆍ허도성FFF 동아대학교 화학과, F동아대학교 의생명과학과, FF동국대학교 생명화학공학과, FFF인제대학교 의생명화학과 (2007년 5월 9일 접수, 2007년 6월 29일 채택) Facile Synthesis of Dendritic Benzyl Chlorides from Their Alcohols with Methanesulfonyl Chloride/Et3N Jae Wook Lee*,7, Seung Choul Han*, Hee Joo Kim, Jung Hwan Kim, Un Yup Lee, Byoung-Ki Kim, Sae Reum Sung, Hwa-Shin Kang, Ji Hyeon Kim**, and Do-Sung Huh*** Department of Chemistry, Dong-A University, Hadan-2-dong, Busan 604-714, Korea *Department of Medical Bioscience, Dong-A University, Hadan-2-dong, Busan 604-714, Korea **Department of Chemical & Biochemical Engineering, Dongguk University, Seoul 100-715, Korea ***Department of Biomedicinal Chemistry, Inje University, Gim Hai 621-749, Korea (Received May 9, 2007; Accepted June 29, 2007) 초록： 덴드리틱 벤질 알코올을 트리에틸아민과 메탄술포닐클로라이드와 반응시켜서, 덴드리틱 벤질 클로라이드 의 효율적인 합성이 이루어졌다. 이 반응은 히드록시기의 메실화 반응과 염소화 반응의 2단계 반응으로 이루어지 는데, 중간체의 분리없이 한 반응 용기내에서 반응이 진행되는 경제적인 방법이다. Abstract： A successful rapid synthesis of dendritic benzyl chlorides from dendritic benzyl alcohols using methanesulfonyl chloride/Et3N as activating agents was described. In this method, each dendritic benzyl chloride can be prepared in one pot: no isolation of intermediate mesylated dendrons is required. The key steps in the syntheses of dendritic benzyl chlorides were the mesylation of the hydroxymethyl group followed by the chlorination by in-situ generated triethylammonium chloride. Keywords： benzylic alcohol, chlorination. Introduction vation and coupling steps in high yield. In addition, the coupling step must be very efficient to enable complete Dendrimers represent a novel type of polymeric material reaction.
    [Show full text]
  • Particularly Hazardous Substances
    Particularly Hazardous Substances In its Laboratory Standard, OSHA requires the establishment of additional protections for persons working with "Particularly Hazardous Substances" (PHS). OSHA defines these materials as "select" carcinogens, reproductive toxins and acutely toxic materials. Should you wish to add: explosive, violently reactive, pyrophoric and water-reactve materials to this category, the information is included. Carbon nanotubes have also been added due to their suspected carcinogenic properties. This table is designed to assist the laboratory in the identification of PHS, although it is not definitively conclusive or entirely comprehensive. *Notes on the proper use of this table appear on page 12. 1 6 5 2 3 4 Substance CAS National Toxicity National Program Carcinogen Toxin Acute Regulated OSHA Carcinogen Group IARC Carcinogen Toxin Reproductive Violently Reactive/ Explosive/Peroxide Forming/Pyrophoric A-a-C(2-Amino-9H-pyrido[2,3,b]indole) 2648-68-5 2B Acetal 105-57-7 yes Acetaldehyde 75-07-0 NTP AT 2B Acrolein (2-Propenal) 107-02-8 AT Acetamide 126850-14-4 2B 2-Acetylaminofluorene 53-96-3 NTP ORC Acrylamide 79-06-6 NTP 2B Acrylyl Chloride 814-68-6 AT Acrylonitrile 107-13-1 NTP ORC 2B Adriamycin 23214-92-8 NTP 2A Aflatoxins 1402-68-2 NTP 1 Allylamine 107-11-9 AT Alkylaluminums varies AT Allyl Chloride 107-05-1 AT ortho-Aminoazotoluene 97-56-3 NTP 2B para-aminoazobenzene 60-09-3 2B 4-Aminobiphenyl 92-67-1 NTP ORC 1 1-Amino-2-Methylanthraquinone 82-28-0 NTP (2-Amino-6-methyldipyrido[1,2-a:3’,2’-d]imidazole) 67730-11-4 2B
    [Show full text]
  • Fragment-Based Discovery of a New Class of Inhibitors Targeting Mycobacterial Trna Modification
    Supplementary Data Fragment-based discovery of a new class of inhibitors targeting mycobacterial tRNA modification Sherine E. Thomas*1, Andrew J. Whitehouse*2, Karen Brown3,4, Juan M. Belardinelli5, Ramanuj Lahiri6, M. Daben J. Libardo7, Pooja Gupta1, Sony Malhotra8, Helena I. M. Boshoff7, Mary Jackson5, Chris Abell 2, Anthony G. Coyne2, Tom L. Blundell §1, R. Andres Floto3,4, Vitor Mendes §1 1 Department of Biochemistry, University of Cambridge, 80 Tennis Court Road, Cambridge CB2 1GA, UK. 2 Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK. 3 MRC Laboratory of Molecular Biology, Francis Crick Avenue, Cambridge, CB2 0QH, U.K. 4 Cambridge Centre for Lung Infection, Royal Papworth Hospital, Cambridge, CB23 3RE, U.K. 5 Mycobacteria Research Laboratories, Department of Microbiology, Immunology and Pathology, Colorado State University, Fort Collins, Colorado, USA. 6 National Hansen’s Disease Program, Healthcare Systems Bureau, HRSA, DHHS, USA 7 Tuberculosis Research Section, Laboratory of Clinical Immunology and Microbiology, National Institute of Allergy and Infectious Disease, National Institutes of Health, 9000 Rockville Pike, Bethesda, Maryland 20892, USA. 8 Birkbeck College, University of London, Malet Street, WC1E7HX, UK * Contributed equally § To whom correspondence should be addressed Results Conservation of catalytic residues in mycobacterial TrmD A multiple sequence alignment of 5 mycobacterial TrmD enzyme sequences with 10 TrmD ortholog amino acid sequences (Figure S1) shows conservation of important catalytic residues and residues involved in tRNA recognition and methyl transfer reactions. The catalytic residues Asp169 and Arg154 are highly conserved across TrmD orthologs. Key residues such as Asp50, Gly59, His46 involved in tRNA G36 and G37 base recognition, interactions with bases at positions 38, 32 and anticodon branch of wild type tRNA respectively, are also broadly conserved.
    [Show full text]
  • 4 Methanesulfonyl Chloride1 Acute Exposure Guideline Levels
    Committee on Acute Exposure Guideline Levels Committee on Toxicology Board on Environmental Studies and Toxicology Division on Earth and Life Studies THE NATIONAL ACADEMIES PRESS 500 FIFTH STREET, NW WASHINGTON, DC 20001 NOTICE: The project that is the subject of this report was approved by the Governing Board of the National Research Council, whose members are drawn from the councils of the National Academy of Sciences, the National Academy of Engineering, and the Insti- tute of Medicine. The members of the committee responsible for the report were chosen for their special competences and with regard for appropriate balance. This project was supported by Contract No. W81K04-11-D-0017 and EP-W-09-007 be- tween the National Academy of Sciences and the U.S. Department of Defense and the U.S. Environmental Protection Agency. Any opinions, findings, conclusions, or recom- mendations expressed in this publication are those of the author(s) and do not necessarily reflect the view of the organizations or agencies that provided support for this project. International Standard Book Number-13: 978-0-309-28308-3 International Standard Book Number-10: 0-309-28308-6 Additional copies of this report are available for sale from the National Academies Press, 500 Fifth Street, NW, Keck 360, Washington, DC 20001; (800) 624-6242 or (202) 334- 3313; http://www.nap.edu/. Copyright 2013 by the National Academy of Sciences. All rights reserved. Printed in the United States of America The National Academy of Sciences is a private, nonprofit, self-perpetuating society of distinguished scholars engaged in scientific and engineering research, dedicated to the furtherance of science and technology and to their use for the general welfare.
    [Show full text]
  • Guide for the Selection of Chemical and Biological Decontamination Equipment for Emergency First Responders
    U.S. Department of Justice Office of Justice Programs National Institute of Justice National Institute of Justice Law Enforcement and Corrections Standards and Testing Program Guide for the Selection of Chemical and Biological Decontamination Equipment for Emergency First Responders NIJ Guide 103–00 Volume I October 2001 ABOUT THE LAW ENFORCEMENT AND CORRECTIONS STANDARDS AND TESTING PROGRAM The Law Enforcement and Corrections Standards and Testing Program is sponsored by the Office of Science and Technology of the National Institute of Justice (NIJ), U.S. Department of Justice. The program responds to the mandate of the Justice System Improvement Act of 1979, which directed NIJ to encourage research and development to improve the criminal justice system and to disseminate the results to Federal, State, and local agencies. The Law Enforcement and Corrections Standards and Testing Program is an applied research effort that determines the technological needs of justice system agencies, sets minimum performance standards for specific devices, tests commercially available equipment against those standards, and disseminates the standards and the test results to criminal justice agencies nationally and internationally. The program operates through: The Law Enforcement and Corrections Technology Advisory Council (LECTAC), consisting of nationally recognized criminal justice practitioners from Federal, State, and local agencies, which assesses technological needs and sets priorities for research programs and items to be evaluated and tested. The Office of Law Enforcement Standards (OLES) at the National Institute of Standards and Technology, which develops voluntary national performance standards for compliance testing to ensure that individual items of equipment are suitable for use by criminal justice agencies.
    [Show full text]
  • Guide for the Selection of Personal Protective Equipment for Emergency First Responders
    U.S. Department of Justice Office of Justice Programs National Institute of Justice National Institute of Justice Law Enforcement and Corrections Standards and Testing Program Guide for the Selection of Personal Protective Equipment for Emergency First Responders NIJ Guide 102–00 Volume I November 2002 U.S. Department of Justice Office of Justice Programs 810 Seventh Street N.W. Washington, DC 20531 John Ashcroft Attorney General Deborah J. Daniels Assistant Attorney General Sarah V. Hart Director, National Institute of Justice For grant and funding information, contact: Department of Justice Response Center 800–421–6770 Office of Justice Programs National Institute of Justice World Wide Web Site World Wide Web Site http://www.ojp.usdoj.gov http://www.ojp.usdoj.gov/nij U.S. Department of Justice Office of Justice Programs National Institute of Justice Guide for the Selection of Personal Protective Equipment for Emergency First Responders NIJ Guide 102-00, Volume I Dr. Alim A. Fatah1 John A. Barrett2 Richard D. Arcilesi, Jr.2 Charlotte H. Lattin2 Charles G. Janney2 Edward A. Blackman2 Coordination by: Office of Law Enforcement Standards National Institute of Standards and Technology Gaithersburg, MD 20899–8102 Prepared for: National Institute of Justice Office of Science and Technology Washington, DC 20531 November 2002 This document was prepared under CBIAC contract number SPO-900-94-D-0002 and Interagency Agreement M92361 between NIST and the Department of Defense Technical Information Center (DTIC). NCJ 191518 1National Institute of Standards and Technology, Office of Law Enforcement Standards. 2Battelle Memorial Institute. National Institute of Justice Sarah V. Hart Director This guide was prepared for the National Institute of Justice, U.S.
    [Show full text]
  • Studies Towards the Synthesis of the Core Structure of Sarains A, B, and C
    T v v O T T V\ v r S - j si V V A ^ O Synthetic Studies Toward^he^Core Structure of Sarains A, B and C A Thesis Presented to the University of London in Partial Fulfilment of the Requirements for the Degree of Doctor of Philosophy Gurdeep Singh Nandra September 2004 Christopher Ingold Laboratories Department of Chemistry University College London London W ClH 0AJ SSSSSSSL ProQuest Number: 10014333 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. uest. ProQuest 10014333 Published by ProQuest LLC(2016). Copyright of the Dissertation is held by the Author. All rights reserved. This work is protected against unauthorized copying under Title 17, United States Code. Microform Edition © ProQuest LLC. ProQuest LLC 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, Ml 48106-1346 Abstract Sarains A-C are marine alkaloids produced by the sponge Reniera sarai, which exhibit antitumor, antibacterial, and insecticidal activities. Sarains A-C have a complex structure, which comprises of a l,5-diazatetracyclo[6.2.1.1^’^.0'^’*^]dodecane tricyclic core surrounded by two macrocycles. To date four groups have communicated the construction of the tricyclic core, however the total synthesis of sarains A-C has yet to be reported. This thesis describes the work undertaken towards the synthesis of a tricycle that contains the core structure of sarains A-C, by the use of a novel carbene mediated ylide rearrangement reaction.
    [Show full text]
  • Sustainable Manufacturing at CABB Chlorination and Sulfonation – Surprisingly Sustainable
    Sustainable manufacturing at CABB Chlorination and sulfonation – surprisingly sustainable Dr. Jörg Schrickel New Business Development, CABB AG RSC Symposium, Budapest, June 18-19, 2014 Sustainable manufacturing Content Introduction . Sustainability, Green Chemistry and metrics . CABB and CABB‘s Verbund and recycling system Case studies: . Mesylation reaction: batch to continuous . Chlorination reaction I: scrubber to Verbund . Chlorination reaction II: continuous and recycling . Sulfonation reaction: Verbund . Amidation reaction: more or less hazardous Conclusion [ 2 ] Sustainable manufacturing Sustainability Economy, Ecology, Society . Efficient, safe and environmentally benign chemical products and processes . Protecting and enhancing human health and the environment . Reducing the environmental impact of processes and products, minimising waste . Extending the quality of life; competitive, knowledge-based, enterprise-led economy Source: OECD [ 3 ] Sustainable manufacturing 12 Principles of Green Chemistry Prevention of waste: It is better to prevent waste than to treat or clean up waste. Atom Economy: Design of synthesis to maximize the incorporation of all materials used in the process into the final product. Less Hazardous Chemical Syntheses: Design of synthesis to use and generate substances that possess little or no toxicity to human health and the environment. Wherever practicable. Designing Safer Chemicals: Design of chemical products to effect their desired function while minimizing their toxicity. Safer Solvents and Auxiliaries:
    [Show full text]
  • Chemical Compatibility Storage Group
    CHEMICAL SEGREGATION Chemicals are to be segregated into 11 different categories depending on the compatibility of that chemical with other chemicals The Storage Groups are as follows: Group A – Compatible Organic Acids Group B – Compatible Pyrophoric & Water Reactive Materials Group C – Compatible Inorganic Bases Group D – Compatible Organic Acids Group E – Compatible Oxidizers including Peroxides Group F– Compatible Inorganic Acids not including Oxidizers or Combustible Group G – Not Intrinsically Reactive or Flammable or Combustible Group J* – Poison Compressed Gases Group K* – Compatible Explosive or other highly Unstable Material Group L – Non-Reactive Flammable and Combustible, including solvents Group X* – Incompatible with ALL other storage groups The following is a list of chemicals and their compatibility storage codes. This is not a complete list of chemicals, but is provided to give examples of each storage group: Storage Group A 94‐75‐7 2,4‐D (2,4‐Dichlorophenoxyacetic acid) 94‐82‐6 2,4‐DB 609-99-4 3,5-Dinitrosalicylic acid 64‐19‐7 Acetic acid (Flammable liquid @ 102°F avoid alcohols, Amines, ox agents see SDS) 631-61-8 Acetic acid, Ammonium salt (Ammonium acetate) 108-24-7 Acetic anhydride (Flammable liquid @102°F avoid alcohols see SDS) 79‐10‐7 Acrylic acid Peroxide Former 65‐85‐0 Benzoic acid 98‐07‐7 Benzotrichloride 98‐88‐4 Benzoyl chloride 107-92-6 Butyric Acid 115‐28‐6 Chlorendic acid 79‐11‐8 Chloroacetic acid 627‐11‐2 Chloroethyl chloroformate 77‐92‐9 Citric acid 5949-29-1 Citric acid monohydrate 57-00-1 Creatine 20624-25-3
    [Show full text]
  • (12) Patent Application Publication (10) Pub. No.: US 2016/0102064 A1 DODDA Et Al
    US 201601 02064A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2016/0102064 A1 DODDA et al. (43) Pub. Date: Apr. 14, 2016 (54) IMPROVED PROCESSES FOR THE Publication Classification PREPARATION OF LINEZOLD USING (51) Int. Cl. NOVELINTERMEDIATES C07D 263/24 (2006.01) C07D 295/135 (2006.01) (71) Applicant: SYMED LABS LIMITED, Hyderabad C07D 209/248 (2006.01) (IN) (52) U.S. Cl. CPC ............ C07D 263/24 (2013.01); C07D 209/48 (72) Inventors: Mohan Rao DODDA, Hyderabad (IN); (2013.01); C07D 295/135 (2013.01) Venkat Reddy BUTHUKURI, (57) ABSTRACT Hyderabad (IN) Provided herein are improved, commercially viable and industrially advantageous processes for the preparation of Linezolid, in high yield and purity, using novel intermediates. (21) Appl. No.: 14/785,960 In one aspect, provided herein are efficient, industrially advantageous and environmentally friendly processes for the (22) PCT Filed: Apr. 25, 2013 preparation of lineZolid, in high yield and with high purity, using novel intermediates. The processes disclosed herein (86). PCT No.: PCT/N2013/000278 avoid the tedious and cumbersome procedures of the prior processes, thereby resolving the problems associated with the S371 (c)(1), processes described in the prior art, which is more convenient (2) Date: Oct. 21, 2015 to operate at lab scale and in commercial scale operations. US 2016/01 02064 A1 Apr. 14, 2016 IMPROVED PROCESSES FOR THE cocci, Vancomycin-resistant enterococci (VRE), and methi PREPARATION OF LINEZOLD USING cillin-resistant Staphylococcus aureus (MRSA). Linezolid is NOVELINTERMEDIATES represented by the following structural formula I: FIELD OF THE INVENTION 0001. The present invention relates to improved, commer cially viable and industrially advantageous processes for the preparation of Linezolid, in high yield and purity, using novel N intermediates.
    [Show full text]
  • A Process for Preparing an Acyl Halide Or Sulfonyl Halide
    ~™ llll III II II III II III I II II III (19) J European Patent Office Office europeen des brevets (1 1 ) EP0 751 131 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int. CI.6: C07D 233/18, C07C 51/60, 02.01.1997 Bulletin 1997/01 C07C 303/02, C07B 41/1 0 (21) Application number: 96108936.4 (22) Date of filing: 04.06.1996 (84) Designated Contracting States: • Hayashi, Hidetoshi DE FR IT NL Ohmuta-shi, Fukuoka-ken, 836 (JP) • Mizuta, Hideki (30) Priority: 20.06.1995 JP 152826/95 Ohmuta-shi, Fukuoka-ken, 837 (JP) (71) Applicant: MITSUI TOATSU CHEMICALS, Inc. (74) Representative: Strehl Schubel-Hopf Groening & Chiyoda-Ku Tokyo 1 00 (JP) Partner Maximilianstrasse 54 (72) Inventors: 80538 Munchen (DE) • Nagata, Teruyuki Ohmuta-shi, Fukuoka-ken, 836 (JP) (54) A process for preparing an acyl halide or sulfonyl halide (57) A preparation process of acyl halide or sulfonyl halide which comprises reacting corresponding carboxylic acid or sulfonic acid with a haloiminium salt represented by the general formula (1): R'-N -R2 X ( 1 ) XCrU/n wherein R1 and R2 are same or different lower alkyl groups, X is a halogen atom, and n is an integer of 2 or 3. CO LO o Q_ LU Printed by Rank Xerox (UK) Business Services 2.13.10/3.4 EP0 751 131 A1 Description 1 . Field of the Invention 5 The present invention relates to a preparation process of acyl halide or sulfonyl halide. 2. Description of the Related Art In recent years, acyl halide has become important in industry as an intermediate for preparing heat resistant resin, 10 medicines and agricultural chemicals.
    [Show full text]