Patent ID: 8557991

Claim:
A process for preparing an enantiomerically pure (stereomerically pure) compound of formula in which R1 is 2-7C-alkyl substituted by —N(R111)R112, R111 is 1-4C-alkyl, 2-4C-alkenyl, 2-4C-alkinyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, 1N-(1-4C-alkyl)-pyrazolyl, 1N—(H)-pyrazolyl, isoxazolyl, or completely or partially fluorine-substituted 1-4C-alkyl, R112 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, or 3-7C-cycloalkyl-1-4C-alkyl, or R111 and R112 together and with inclusion of the nitrogen atom, to which they are bonded, form a ring Het, Het is piperidin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, S-oxo-thiomorpholin-4-yl, S,S-dioxo-thiomorpholin-4-yl, pyrrolidin-1-yl, azetidin-1-yl, homopiperidin-1-yl, 4N—(R113)-piperazin-1-yl, 4N—(R113)-homopiperazin-1-yl, 2,5-dihydro-pyrrol-1-yl, 1,2,3,6-tetra-hydropyridin-1-yl, pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, triazol-1-yl, or tetrazol-1-yl, wherein said Het may be optionally substituted by one or two substituents independently selected from fluorine and 1-4C-alkyl, R113 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkylcarbonyl, amidino, or completely or partially fluorine-substituted 1-4C-alkyl, R2 is hydrogen, 1-4C-alkyl, halogen trifluoromethyl, 1-4C-alkoxy or hydroxyl, R3 is hydrogen, 1-4C-alkyl, halogen, trifluoromethyl or 1-4C-alkoxy, R4 is 1-4C-alkyl, 3-7C-cycloalkyl or 3-7C-cycloalkyl-1-4C-alkyl, R5 is 1-4C-alkyl, halogen, 1-4C-alkoxy, trifluoromethyl, cyano, hydroxyl, phenyl-1-4C-alkoxy, 1-4C-alkoxy-2-4C-alkoxy, hydroxy-2-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkyl-1-4C-alkoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy, and R6 is hydrogen, 1-4C-alkyl or halogen, or a salt thereof which process comprises c) optionally protecting the compound of formula IIa wherein R, R2, R3, R4, R5, and R6 are as defined above, at the 3-hydroxyphenyl moiety to obtain a compound of formula IIa*, wherein R, R2, R3, R4, R5, and R6 are as defined above and Z is a protective group, d) heterocyclizing the compound of formula IIa* or the compound of formula IIa by in situ prepared isocyanate R1-N═C═O by adding a reaction mixture of carbonyldiimidazole and an amine R1NH 2 in a solvent selected from the group consisting of toluene, xylene, a mixture of toluene and acetonitrile and a mixture of toluene and benzonitrile to obtain a compound of formula Ia, wherein R1-R6 and Z are as defined above, or to obtain the compound of formula I, and e) deprotecting the 3-hydroxyphenyl moiety of the compound of formula Ia to obtain the compound of formula I, provided that the compound of formula IIa have been protected at the 3-hydroxyphenyl moiety in c).