Patent ID: 7105663

Claim:
A process for preparing a compound of formula I: wherein each of R 1 and R 2 independently represents a C 1-6 alkyl or C 2-7 acyl group; R 5 represents a hydrogen atom or a C 1-3 alkyl, C 2-3 alkenyl or C 2-3 alkynyl group; R 6 represents a hydrogen atom or a C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, amino, C 1-6 alkylamino, di(C 1-6 )alkylamino or C 2-7 acylamino group; each of R 7 and R 8 independently represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 2-7 acyl, C 1-6 alkylthio, C 1-6 alkoxy, C 3-6 cycloalkyl; and R 9 represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 2-7 acyl, C 1-6 alkylthio, C 1-6 alkoxy or C 3-6 cycloalkyl group; X represents a group CR 3 R 4 , wherein each of R 3 and R 4 independently represents a hydrogen atom or a C 1-3 alkyl group; each of R 10 and R 11 independently represents a hydrogen atom, a C 1-3 alkyl, C 3-6 cycloalkyl or phenyl group; Y represents an oxygen atom or a group CHNO 2 , NCN, NH or NNO 2 ; n is an integer from 2 to 4; or a salt thereof, the process comprising: (a) reacting a compound of formula II: wherein R 1 , R 2 , R 5 , R 6 , R 7 , R 8 , R 9 , X and n are as defined for formula I, with an amine-reactive compound selected from the group consisting of (i) a cyanate salt, (ii) an isocyanate of the formula R 11 —NCO wherein R 11 is as defined for formula I, (iii) an N—C 1-3 alkyl- or N—C 3-6 cycloalkyl-1-methylthio)-2-nitroethenamine of the formula CH 3 SC(═CHNO 2 )NR 10 R 11 wherein R 10 and R 11 are as defined for formula I, (iv) a compound of the formula CH 3 SC(═NH)NR 10 R 11 or a salt thereof wherein R 10 and R 11 are as defined for formula I, (v) a compound of the formula CH 3 SC(═NCN)NR 10 R 11 or a salt thereof wherein R 10 and R 11 are as defined for formula I, and (vi) 2-methyl-1-nitro-2-isothiourea, to form a compound of formula I; or (b) reacting a compound of formula II as defined in (a) with 1,1-bis(methylthio)-2-nitroethylene and reacting the resulting compound with an amine of the formula R 10 R 11 NH wherein R 10 and R 11 are as defined for formula I, to form a compound of formula I; or (c) reacting a compound of formula II as defined in (a) with N,N′-1,3-di-(tert-butoxycarbonyl)thiourea and treating the resulting compound with trifluoroacetic acid, to form a compound of formula I: or (d) reacting a compound of formula II as defined in (a) with dimethyl-N-cyanodithioiminocarbonate and reacting the resulting compound with an amine of the formula R 10 R 11 NH wherein R 10 and R 11 are as defined for formula I, to form a compound of formula I; or (e) when X in formula I represents a group CR 3 R 4 , wherein R 3 represents a hydrogen atom, R 4 represents a hydrogen atom or a C 1-3 alkyl group, and R 5 represents a hydrogen atom or a C 1-3 alkyl group, hydrogenating a compound of formula III: wherein R 1 , R 2 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , Y and n are as defined for formula I.