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【结 构 式】

【分子编号】69265

【品名】(2R,11aS,12aR,14aR)-2-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)-5-methyl-4,14-dioxo-1,2,3,3a,4,5,6,7,8,9,11a,12,12a,13,14,14a-hexadecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a-carboxylic acid

【CA登记号】 

【 分 子 式 】C35H42N4O6S

【 分 子 量 】646.808

【元素组成】C 64.99% H 6.54% N 8.66% O 14.84% S 4.96%

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:(III)

Ring closing metathesis of intermediate (I) by means of Hoveyda–Grubbs first-generation catalyst in 1,2-dichloroethane at 75 °C furnishes macrocycle (II), which is then treated with LiOH in THF/MeOH/H2O to give carboxylic acid (III). Finally, activation of acid (III) by treatment with 1,1’-carbonyldiimidazole (CDI) in refluxing THF affords the oxazolidinedione derivative (IV), which is readily reacted with cyclopropylsulfonamide (V) in the presence of DBU in THF at 50 °C .

1 Raboisson, P., De Kock, H., Rosenquist, A. et al. Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350. Bioorg Med Chem Lett 2008, 18(17): 4853-8.
2 Stokbroekx, S.C.M., Leys, C., Swinney, K.A., Wuyts, S., Horvath, A. (Tibotec Pharmaceuticals Ltd.). Polymorphic forms of a macrocyclic inhibitor of HCV. WO 2008092954.
3 Raboisson, P.J.-M.B., De Kock, H.A., Hu, L. et al. (Tibotec Pharmaceuticals Ltd.; Medivir AB). Macrocyclic inhibitors of hepatitis C virus. CA 2616580, EP 1912999, JP 2009502889, WO 2007014926.
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) 69263 (1S,2R)-ethyl 1-((1S,2S,4S)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate   C39H50N4O6S 详情 详情
(II) 69264 (3aS,11aR,12aS,14aS)-ethyl 2-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)-5-methyl-4,14-dioxo-1,2,3,3a,4,5,6,7,8,9,11a,12,12a,13,14,14a-hexadecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a-carboxylate   C37H46N4O6S 详情 详情
(III) 69265 (2R,11aS,12aR,14aR)-2-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)-5-methyl-4,14-dioxo-1,2,3,3a,4,5,6,7,8,9,11a,12,12a,13,14,14a-hexadecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a-carboxylic acid   C35H42N4O6S 详情 详情
(IV) 69266 (1aS,11S,12aR,17aR)-11-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)-8-methyl-1,1a,5,6,7,8,10,11,12,12a-decahydrocyclopenta[c]cyclopropa[g]oxazolo[3,4-f][1,6]diazacyclotetradecine-9,13,15,17(4H,9aH)-tetraone   C36H40N4O7S 详情 详情
(V) 68242 cyclopropanesulfonamide;Cyclopropanesulfonyl amide 154350-29-5 C3H7NO2S 详情 详情
Extended Information