Patent IL-134322-A (IL)
Title: Process for the preparation of formamide intermediates for the preparation of imidazole compounds
IPC: C07D401/12
Filed: 1995-12-19
Abstract: A process for preparing a compound of the formula: wherein p is 0, or 2; Ar is an optionally substituted phenyl or naphthyl; R4 is phenyl, naphth-1-yl, naphth-2-yl, or a heteroaryl, which is optionally substituted by one or two substituents, each of which is independently selected, and which, for a 4-phenyl, 4-naphth-1-yl or 6-naphth-2-yl substituent, is halogen, cyano, nitro, C(Z)NR7R17, C(Z)OR16, (CR10R20)v COR12, SR5, SOR5, OR12, halo-substituted C1-4 alkyl, C1-4 alkyl, ZC(Z)R12, NR10C(Z)R16, or (CR10R20)v NR10R20 and which, for other 2286 כ" ה באלול התשס" א - September 13, 2001 positions of substitution, is halogen, cyano, C(Z)NR13R14, C(Z)OR3, (CR10R20)m " COR3, S(O)mR3, OR3, halo-substituted C-4 alkyl, C1-4 alkyl, (CR10R20)m " NR10C(Z)R3, NR10S(O)m' R8, NR10 S(O)m 'NR7R17, ZC(Z)R3 or (CR10R20)m" NR13R11; Z is oxygen or sulfur; v is 0, or an integer having a value of 1 or 2; m is 0, or the integer 1 or 2; m' is an integer having a value of 1 or 2, m" is 0, or an integer having a value of 1 to 5; n is an integer having a value of 1 to 10; R3 is heterocyclyl, heterocyclyl C1-10 alkyl or R8; R5 is hydrogen, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl or NR7R17, excluding the moieties -SR5 being -SNR7R17 and -SOR5 being -SOH; R7 and R17 is each independently selected from hydrogen or C1-4 alkyl or R7 and R17 together with the nitrogen to which they are attached form a heterocyclic ring of 5 to 7 members which ring optionally contains an additional heteroatom selected from oxygen, sulfur or NR15; R8 is C1-10 alkyl, halo-substituted C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-7 cycloalkyl, C5-7 cycloalkenyl, aryl, aryl C1-10 alkyl, heteroaryl, heteroaryl C1-10 alkyl, (CR10R20)nOR11, (CR10R20)n S(O)mR18, (CR10R20)nNHS(O)2R18, (CR10R20)n NR13R14; wherein the aryl, arylalkyl, heteroaryl, heteroaryl alkyl may be optionally substituted; R9 is hydrogen, -C(Z)R11 or optionally substituted C1-10 alkyl, S(O)2R18, optionally subsituted aryl or optionally substituted aryl- C1-4 alkyl; R10 and R20 is each independently selected from hydrogen or C1-4 alkyl; R11 is hydrogen, C1-10 alkyl, C3-7 cycloalkyl, heterocyclyl, heterocyclyl C1-10 alkyl, aryl, aryl C1-10 alkyl, heteroaryl or heteroaryl C1-10 alkyl; R12 is hydrogen or R16; R13 and R14 is each independently selected from hydrogen or optionally substituted CGd21-Gd24 alkyl, optionally substituted alkyl, optionally substituted aryl or optionally substituted aryl-C1-4 alkyl, or together with the nitrogen to which they are attached form a heterocyclic ring of 5 to 7 members which ring optionally contains an additional heteroatom selected from oxygen, sulfur or NR9; R15 is R10 or C(Z)-C1-4 alkyl; R16 is C1-4 alkyl, halo-substituted-C1-4 alkyl, or C3-7 cycloalkyl; R18 is C1-10 alkyl, C3-7 cycloalkyl, heterocyclyl, aryl, arylalkyl, heterocyclyl, heterocyclyl-C1-10 alkyl, heteroaryl or heteroarylalkyl; which process comprises reacting together an aldehyde of the formula: R4-CHO a compound of the formula: ArS(O)pH, wherein Ar is an optionally substituted phenyl or naphthyl, and p is 0, or 2; with formamide, a dehydrating agent, and optionally an acid catalyst to yield a compound of Formula (IV). 2287 כ" ה באלול התשס" א - September 13, 2001