Method of manufacturing the cycloheptimidazole derivatives

• Main Authors: TOMIYAMA, TAKESHI, TOMIYAMA, ITARU, YANAGISAWA, TAKASHI
• Format: Patent
• Language: English
• Published: 11.10.2000
• Edition: 7
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS

A method of preparing a compound of general formula (4) where in R1 is hydrogen or isopropyl; R2 represents a chain or branched C1-C4alkyl; (i) when A and A1 are individually bound at 4- or 8- position, A is a hydrogen and A1 is a hydrogen atom or hydroxy group, or (ii) when A and A1 are simultaneously bound at 4- or 8- position, A and A1 together form an oxo group (=0) or =CHCOOR' (R' represents a chain or branched C1-C4alkyl); line is saturated single bond; which comprises reacting a compound of general formula (1) wherein R1, R2, A, A1, line are as defined above, X is halogen atom or trifluoromethanesulfonate; with a compound of general formula (2) by known method wherein Y is -B(OH)2 or -Sn(R5)3 (R5 represents a chain or branched C1-C4alkyl); Z is a protecting group selected from the group consisting of t-butyl, trithyl (-C(Ph)3), methoxymethylether, benzylmethylether and -nitrophenyl; to give a compound of general formula (3) wherein R1, R2, A, A1, line and Z are as defined above; the compound (3) is following deprotected with HCl or CH3SO3H in the presence of organic solvent(s) at reflux to give the compound of general formula (4).