Patent RU-2431630-C2 (RU)
Title: Method of producing biarylurea and analogues thereof
Inventor: EHNSELL GREHKHEM
IPC: C07C271/34
Filed: 2006-05-09
Granted: 2011-10-20
Abstract: FIELD: chemistry. 
     SUBSTANCE: invention relates to a method of producing a compound of formula I:   or salt thereof, where: y equals 0; R 1  and R 2  are taken together to form a 3-tetrahydrofuran ring; R 9  is hydrogen; R 10  is 5-oxazolyl; R 11  is a methoxy-, ethoxy- or isopropoxy group; each V 1  is independently selected from halogen, NO 2 , CN, OR 12 , OC(O)R 13 , OC(O)R 12 , OC(O)OR 13 , OC(O)OR 12 , OC(O)N(R 13 ) 2 , OP(O)(OR 13 ) 2 , SR 13 , SR 12 , S(O)R 13 , S(O)R 12 , SO 2 R 13 , SO 2 R 12 , SO 2 N(R 13 ) 2 , SO 2 NR 12 R 13 , SO 3 R 13 , C(O)R 12 , C(O)OR 12 , C(O)R 13 , C(O)OR 13 , NC(O)C(O)R 13 , NC(O)C(O)R 12 , NC(O)C(O)OR 13 , NC(O)C(O)N(R 13 ) 2 , C(O)N(R 13 ) 2 , C(O)N(OR 13 )R 13 , C(O)N(OR 13 )R 12 , C(NOR 13 )R 13 , C(NOR 13 )R 12 , N(R 13 ) 2 , NR 13 C(O)R 12 , NR 13 C(O)R 13 , NR 13 C(O)OR 13 , NR 13 C(O)OR 12 , NR 13 C(O)N(R 13 ) 2 , NR 13 C(O)NR 12 R 13 , NR 13 SO 2 R 13 , NR 13 SO 2 R 12 , NR 13 SO 2 N(R 13 ) 2 , NR 13 SO 2 NR 12 R 13 , N(OR 13 )R 13 , N(OR 13 )R 12 , P(O)(OR 13 )N(R 13 ) 2  and P(O)(OR 13 ) 2 ; where each R 12  is a monocyclic or bicyclic ring system consisting of 5-6 members in each ring, where said ring system optionally contains up to 4 heteroatoms selected from N, O or S, and where CH 2  lying next to said N, O or S can be substituted with C(O); and each R 12  optionally contains up to 3 substitutes selected from R 11 ; where each R 13  is independently selected from H, (C 1 -C 4 )-straight or branched alkyl or (C 2 -C 4 )-straight or branched alkenyl; and where each R 13  optionally contains a substitute which is R 14 ; where R 14  is a monocyclic or bicyclic ring system consisting of 5-6 members in each ring, where said ring system optionally contains up to 4 heteroatoms selected from N, O or S, and where CH 2  lying next to said N, O or S can be substituted with C(O); and each R 14  optionally contains up to 2 substitutes independently selected from H, (C 1 -C 4 )-straight or branched alkyl or (C 2 -C 4 )-straight or branched alkenyl, 1,2-methylenedioxy-, 1,2-ethylenedioxy group or (CH 2 ) n -Z; where Z is selected from halogen, CN, NO 2 , CF 3 , OCF 3 , OH, S(C 1 -C 4 )alkyl, SO(C 1 -C 4 )alkyl, SO 2 (C 1 -C 4 )alkyl, NH 2 , NH(C 1 -C 4 )-alkyl, M((C 1 -C 4 )alkyl) 2 , COOH, C(O)O(C 1 -C 4 )alkyl or O(C 1 -C 4 )-alkyl; and where any carbon atom in any R 13  is optionally substituted with O, S, SO, SO 2 , NH or N(C 1 -C 4 )alkyl; where said method includes a step for reacting a compound of formula II with a compound of formula III in a polar or nonpolar aprotic, virtually anhydrous solvent or mixture thereof, and optionally in an acceptable base selected from an organic base, inorganic base or a combination of an organic base and an inorganic base; and while heating the reaction mixture to temperature ranging from approximately 30°C to approximately 180°C for approximately 1 to 48 hours in a virtually inert atmosphere:   where: LG is -OR 16 ; where R 16  is -(C 1 -C 6 )-straight or branched alkyl; -(C 2 -C 6 )-straight or branched alkenyl or alkynyl; or a monocyclic ring system consisting of 5-6 members in each ring, where said ring system optionally contains up to 3 heteroatoms selected from N, O or S, and each R 16  optionally contains up to 5 substitutes independently selected from (C 1 -C 4 )-straight or branched alkyl, (C 2 -C 4 )-straight or branched alkenyl or (CH 2 ) n -Z; n equals 0, 1, 2, 3 or 4; V 1 , y, Z, R 1 , R 2 , R 9 , R 10  and R 11  are as indicated above; and provided that R 16  is not a halogen-substituted (C 2 -C 3 )-straight alkyl. 
     EFFECT: improved method. 
     19 cl, 1 ex