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(12) United States Patent (10) Patent No.: US 8,026,396 B2 Mitsuda Et Al

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(12) United States Patent (10) Patent No.: US 8,026,396 B2 Mitsuda Et Al USOO8026396 B2 (12) United States Patent (10) Patent No.: US 8,026,396 B2 Mitsuda et al. (45) Date of Patent: Sep. 27, 2011 (54) PROCESSES FOR THE PREPARATION OF E. E. 1886 OPTICALLY ACTIVE INTERMEDIATES EP 1418168 5, 2004 WO O 1922.63 12/2001 (75) Inventors: Masaru Mitsuda, Osaka (JP); Tadashi Moroshima, Osaka (JP); Kentaro OTHER PUBLICATIONS Tsukuya, Osaka (JP); Kazuhiko Office Action dated Dec. 30, 2009 received in copending U.S. Appl. Watabe, Osaka (JP); Masahiko No. 1 1/833,263. Yamada, Osaka (JP) Tomoskozi. Tetrahedron (1963) 19(12): 1969-1979 Abstract. Office Action dated Apr. 23, 2009 received in copending U.S. Appl. (73) Assignee: AstraZeneca AB, Sodertalje (SE) No.Engel 1 1/833,263.et al., “Photochemistry of azocyclopropane.” J Org Chem (*) Notice: Subject to any disclaimer, the term of this ECS1988) 53(2O):4748-4758. STN. Acc. No. 1971:435269, Filler et al., J. patent is extended or adjusted under 35 Chem. Soc., Section C: Organic (1971), 11, p. 2062-2068 (abstract). U.S.C. 154(b) by 0 days. Yasuri et al., “Vibrational circular dichroism of optically active cyclopropanes. 3. trans-2-Phenylcyclopropanecarboxylic acid (21) Appl. No.: 12/854,215 derivatives and related compounds.” J Am Chem Soc (1987) 109(8):2311-2320. (22) Filed: Aug. 11, 2010 Armstrong et al., “Stereocontrolled synthesis of 3-(trans-2- aminocyclopropyl)alanine, a key component of belactosin A.” (65) Prior Publication Data Organic Letters (2003) 5(13):2331-2334. Barbieri et al., “Chemo-enzymatic synthesis of (R)- and (S)-3,4- US 2010/0331575A1 Dec. 30, 2010 dichlorophenylbutanolide intermediate in the synthesis of sertraline.” Tetrahedron: Asymmetry (1999) 10:3931-3937. Related U.S. Application Data Wang et al., “Enantioselective synthesis of chiral cyclopropane com pounds through microbial transformations of trans-2- (63) Continuation of application No. 1 1/833.266, filed on arylcyclopropanecarbonitriles.” Tetrahedron Letters (2000)41:6501 Aug. 3, 2007, now Pat. No. 7,790,927. 6505. White “New reactions of polyfluoroaromatic compounds. Part II. (30) Foreign Application Priority Data Polyfluoroaralkyl amines.” J. ChemSoc. (1971) 2062-2068. Singh et al., “Development of a practical, safe, and high-yielding Aug. 5, 2006 (GB) ................................... O61562O2 process for the preparation of enationerically pure trans cyclopropane carboxylic acid.” Organic Process Research & Devel (51) Int. Cl. opment (2002) 6:618-620. C07C 233/58 (2006.01) Notice of Allowance dated Sep. 7, 2010 received in copending U.S. (52) U.S. Cl. ........................................ 564/161; 564/190 Appl. No. 1 1/833,263. (58) Field of Classification Search ........................ None * cited by examiner See application file for complete search history. Primary Examiner — Brian J Davis (56) References Cited (74) Attorney, Agent, or Firm — Pepper Hamilton LLP U.S. PATENT DOCUMENTS (57) ABSTRACT 4411,925. A 10/1983 Brennan et al. This invention relates to processes for the production of opti 4,590,292 A 5, 1986 Blackwell et al. 4.933.477 A 6, 1990 Goetz et al. cally active 2-(disubstituted aryl)cyclopropylamine com 5,225.602 A 7, 1993 Hoelderich et al. pounds and optically active 2-(disubstituted aryl)cyclopro 5,728,873 A 3, 1998 Kleemiss et al. pane carboxamide compounds which are useful 3. 4.58. St. intermediates for the preparation of pharmaceutical agents, ww- oeller et al. and in particular the compound 1S-(1C.2O.3f3(1S,2R), 7,790,927 B2 ck 9/2010 Mitsuda et al. ............... 564,307 5 B)-3-7-2-(3,4-difluorophenyl)-cyclopropylamino-5- FOREIGN PATENT DOCUMENTS (propylthio)-3H-1,2,3-triazolo 4,5-dipyrimidin-3-yl)-5-(2- DE 3909142 10, 1990 hydroxyethoxy)-cyclopentane-1,2-diol. DE 4315623 11, 1994 DE 19523868 1, 1997 2 Claims, No Drawings US 8,026,396 B2 1. 2 PROCESSES FOR THE PREPARATION OF (v) A process to obtain optically active cyclopropanecar OPTICALLY ACTIVE INTERMEDIATES boxylic acid derivative by cyclopropanation after deriving into optically active ester or amide via several steps using CROSS-REFERENCE TO RELATED benzaldehyde derivative as the starting material (WO01/ APPLICATIONS 92263); and (vi) A process to obtain optically active 2-dihydrofuranyl This application is a continuation of U.S. Ser. No. 1 1/833, cyclopropanecarboxylate derivative by reacting phospho 266 filed Aug. 3, 2007, which claims priority to Great Britain noacetic acid ester derivative with optically active dihy Application No. 0615620.2 filed Aug. 5, 2006, each of which drobenzofuranyl ethylene oxide derivative in the presence of is incorporated herein by reference in its entirety. 10 base (Organic Process Research & Development, Vol 6, p. 618 (2002)). FIELD OF THE INVENTION Examples of a process to produce optically active 2-aryl This invention relates to processes for the production of cyclopropylamine derivatives from optically active 2-aryl optically active 2-(disubstituted aryl)cyclopropylamine 15 cyclopropanecarboxylic acid are: derivatives and optically active 2-(disubstituted aryl)cyclo (vii) A process whereinbenzaldehydes is used as the start propane carboxamide derivative which are useful intermedi ing material and derived into optically active ester or amide ates for the preparation of pharmaceutical agents, and in via several steps, and thereafter optically active 2-aryl cyclo particular the compound 1S-(1C.2O.3 B(1S,2R).5B)-3- propane carboxylate ester is obtained by cyclopropanation. 7-2-(3,4-difluorophenyl)-cyclopropylamino-5-(propy This optically active carboxylic acid derivative is formed into lthio)-3H-1,2,3-triazolo 4.5-dpyrimidin-3-yl)-5-(2-hy acid azide, and optically active 2-aryl cyclopropylamine droxyethoxy)-cyclopentane-1,2-diol. This compound, and derivative is produced by Curtius rearrangement (WO01/ similar such compounds, are disclosed in WO 00/34283 and 92263). WO99/05143. These compounds are disclosed as P. (which In the process for the production of optically active 2-aryl is now usually referred to as PY) receptor antagonists. 25 cyclopropane carboxamides referred to in (i) above, only the Such antagonists can be used as, interalia, inhibitors of plate process to produce 2-phenylcyclopropane carboxamide from let activation, aggregation or degranulation. 2-phenylcyclopropane carboxylic acid is described and a pro cess for production for 2-(disubstituted aryl)cyclopropane BACKGROUND OF THE INVENTION carboxamide derivative is not disclosed. Moreover, in the 30 process (ii) above, there is mentioned the process for produc Some processes are known for the production of optically tion only of 2,2-dimethyl-3-phenylcyclopropane carboxam active 2-cyclopropane carboxamide derivatives, optically ide and 2,2-dimethyl-3-isopropylidene cyclopropane car active 2-aryl cyclopropylamine derivatives, and optically boxamide, and a process for production of 2-(disubstituted active 2-arylcyclopropane-1-carboxylate ester derivatives. aryl)cyclopropane carboxamide derivative is not disclosed. Examples of processes for the production of optically 35 Secondly, in a process for the production of optically active active 2-arylcyclopropane carboxamide derivatives are: 2-aryl cyclopropylamine derivative, optically active 2-aryl (i) A process wherein excess thionyl chloride is reacted cyclopropylamine derivative is produced by Curtius rear with optically active 2-phenylcyclopropane carboxylic acid rangement from optically active 2-arylcyclopropane car in benzene solvent to form corresponding acid chloride, and boxylic acid in the aforesaid process (iii), however, it is not after concentrating down excess thionyl chloride and benzene 40 suitable for a commercial preparation method from the view under reduced pressure, the acid chloride is isolated and point of safety because it is via an acid azide intermediate purified by distillation, and, by causing ammonia water to act having explosive properties. Moreover, in the process (iv), on this, 2-phenylcyclopropane carboxamide is obtained (J. optically active amine is produced from the optically active Am. Chem. Soc. Vol. 109, p. 2311 (1987), Journal of Medici carboxamide by a Hofmann rearrangement. However, it is not nal Chemistry Vol. 20, p. 771 (1977)); and 45 suitable for a commercial preparation method from the view (ii) A Process to obtain optically active 3-aryl-2-dimethyl point of economy because yield is low when the reaction is cyclopropane-1-carboxamide by causing ammonia water to carried out using the Sodium hypochlorite. Moreover, as for act on the corresponding acid chloride formed by reacting the aforesaid process (iv), only the process to produce opti thionyl chloride with optically active 3-aryl-2-dimethylcy cally active 2,2-dimethyl cyclopropylamine from optically clopropane-1-carboxylic acid (J. Org. Chem. Vol. 68, p. 621 50 active 2,2-dimethylcyclopropane carboxamide is mentioned, (2003)). and a process for production of 2-(disubstituted aryl)cyclo Examples of processes for the production of optically propane carboxamide derivative is not disclosed. active 2-aryl cyclopropylamine derivatives are: Thirdly, in a process for the production of optically active (iii) A process wherein chlorocarbonic acid ethyl ester is 2-arylcyclopropane carboxylate ester derivative, in the afore reacted with 2-aryl cyclopropane carboxylic acid to form 55 said process (V), optically active 3,4-difluorophenyl cyclo mixed acid anhydride, and by causing to act Sodium azide on propanecarboxylic derivative is obtained by cyclopropana this, corresponding acid azide is formed, and 2-aryl cyclopro tion after converting 3,4-difluoro benzaldehyde
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