METHOD OF PRODUCING BIARYLUREA AND ANALOGUES THEREOF Russian patent published in 2011 - IPC C07C275/42 C07D307/16 C07D413/12 C07C271/34 C07C273/18 

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing a compound of formula I: or salt thereof, where: y equals 0; R¹ and R² are taken together to form a 3-tetrahydrofuran ring; R⁹ is hydrogen; R¹⁰ is 5-oxazolyl; R¹¹ is a methoxy-, ethoxy- or isopropoxy group; each V¹ is independently selected from halogen, NO², CN, OR¹², OC(O)R¹³, OC(O)R¹², OC(O)OR¹³, OC(O)OR¹², OC(O)N(R¹³)₂, OP(O)(OR¹³)₂, SR¹³, SR¹², S(O)R¹³, S(O)R¹², SO₂R¹³, SO₂R¹², SO₂N(R¹³)₂, SO₂NR¹²R¹³, SO₃R¹³, C(O)R¹², C(O)OR¹², C(O)R¹³, C(O)OR¹³, NC(O)C(O)R¹³, NC(O)C(O)R¹², NC(O)C(O)OR¹³, NC(O)C(O)N(R¹³)₂, C(O)N(R¹³)₂, C(O)N(OR¹³)R¹³, C(O)N(OR¹³)R¹², C(NOR¹³)R¹³, C(NOR¹³)R¹², N(R¹³)₂, NR¹³C(O)R¹², NR¹³C(O)R¹³, NR¹³C(O)OR¹³, NR¹³C(O)OR¹², NR¹³C(O)N(R¹³)₂, NR¹³C(O)NR¹²R¹³, NR¹³SO₂R¹³, NR¹³SO₂R¹², NR¹³SO₂N(R¹³)₂, NR¹³SO₂NR¹²R¹³, N(OR¹³)R¹³, N(OR¹³)R¹², P(O)(OR¹³)N(R¹³)₂ and P(O)(OR¹³)₂; where each R¹² 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 CH₂ lying next to said N, O or S can be substituted with C(O); and each R¹² optionally contains up to 3 substitutes selected from R¹¹; where each R¹³ is independently selected from H, (C₁-C₄)-straight or branched alkyl or (C₂-C₄)-straight or branched alkenyl; and where each R¹³ optionally contains a substitute which is R¹⁴; where R¹⁴ 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 CH₂ lying next to said N, O or S can be substituted with C(O); and each R¹⁴ optionally contains up to 2 substitutes independently selected from H, (C₁-C₄)-straight or branched alkyl or (C₂-C₄)-straight or branched alkenyl, 1,2-methylenedioxy-, 1,2-ethylenedioxy group or (CH₂)_n-Z; where Z is selected from halogen, CN, NO₂, CF₃, OCF₃, OH, S(C₁-C₄)alkyl, SO(C₁-C₄)alkyl, SO₂(C₁-C₄)alkyl, NH₂, NH(C₁-C₄)-alkyl, M((C₁-C₄)alkyl)₂, COOH, C(O)O(C₁-C₄)alkyl or O(C₁-C₄)-alkyl; and where any carbon atom in any R¹³ is optionally substituted with O, S, SO, SO₂, NH or N(C₁-C₄)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 -OR¹⁶; where R¹⁶ is -(C₁-C₆)-straight or branched alkyl; -(C₂-C₆)-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 R¹⁶ optionally contains up to 5 substitutes independently selected from (C₁-C₄)-straight or branched alkyl, (C₂-C₄)-straight or branched alkenyl or (CH₂)_n-Z; n equals 0, 1, 2, 3 or 4; V¹, y, Z, R¹, R², R⁹, R¹⁰ and R¹¹ are as indicated above; and provided that R¹⁶ is not a halogen-substituted (C₂-C₃)-straight alkyl.

EFFECT: improved method.

19 cl, 1 ex