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【结 构 式】

【分子编号】46723

【品名】6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-2(1H)-quinolinone

【CA登记号】

【 分 子 式 】C22H13Cl2NO2

【 分 子 量 】394.25616

【元素组成】C 67.02% H 3.32% Cl 17.98% N 3.55% O 8.12%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(V)

Cyclization of 3-(3-chlorophenyl)-N-phenyl-2-propenamide (I) by means of polyphosphoric acid (PPA) at 100 C gives 4-(3-chlorophenyl)-1,2,3,4-tetrahydroquinolin-2-one (II), which is condensed with 4-chlorobenzoic acid (III) by means of PPA at 140 C to yield 6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-1,2,3,4-tetrahydroquinolin-2-one (IV). The dehydrogenation of (IV) by means of Br2 in bromobenzene at 160 C affords 6-(4-chlorobenzoyl)-4-(3-chlorophenyl)quinolin-2(1H)-one (V), which is methylated with iodomethane and NaOH/benzyltrimethylammonium chloride in THF to provide 6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-1-methylquinolin-2(1H)-one (VI). Condensation of compound (VI) with 1-methylimidazole (VII) by means of butyllithium in THF gives the triaryl carbinol (VIII), which is finally treated with ammonia in THF to afford R-115777.

1 Sorbera, L.A.; Castaner, J.; Fernandez, R.; R-115777. Drugs Fut 2001, 26, 5, 453.
2 Venet, M.G.; Angibaud, P.R.; Muller, P.; Sanz, G.C. (Janssen Pharmaceutica NV); Farnesyl protein transferase inhibiting (imidazol-5-yl)methyl-2-quinolinone derivs.. EP 0865440; JP 1998511405; US 6037350; WO 9721701 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 46720 (E)-3-(3-chlorophenyl)-N-phenyl-2-propenamide C15H12ClNO 详情 详情
(II) 46721 4-(3-chlorophenyl)-3,4-dihydro-2(1H)-quinolinone C15H12ClNO 详情 详情
(III) 18359 p-chlorobenzoic acid; 4-chlorobenzoic acid 74-11-3 C7H5ClO2 详情 详情
(IV) 46722 6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-3,4-dihydro-2(1H)-quinolinone C22H15Cl2NO2 详情 详情
(V) 46723 6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-2(1H)-quinolinone C22H13Cl2NO2 详情 详情
(VI) 46724 6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone C23H15Cl2NO2 详情 详情
(VII) 38630 1-methyl-1H-imidazole 616-47-7 C4H6N2 详情 详情
(VIII) 46725 4-(3-chlorophenyl)-6-[(4-chlorophenyl)(hydroxy)(1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone C27H21Cl2N3O2 详情 详情
Extended Information