• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】63495

【品名】methyl 2-(2-{[(4-fluorophenyl)methyl]sulfanyl}-4-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-1-yl)acetate

【CA登记号】

【 分 子 式 】C17H17FN2O3S

【 分 子 量 】348.3980632

【元素组成】C 58.61% H 4.92% F 5.45% N 8.04% O 13.78% S 9.2%

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:(X)

Condensation between ethyl 2-oxocyclopentanecarboxylate (I) and thiourea (II) gives rise to the thiouracil derivative (III) (1,2). This is then alkylated with 4-fluorobenzyl chloride (IV) to yield thioether (V). Subsequent alkylation of (V) with tert-butyl iodoacetate (VI) furnishes adduct (VII). Further acidic cleavage of the tert-butyl ester group of (VII) leads to carboxylic acid (VIII) (2,3). Alternatively, intermediate (VIII) is prepared by alkylation of (V) with triflate (IX), followed by alkaline hydrolysis of the resultant methyl ester (X)

1 The identification of clinical candidate SB-480848: A potent inhibitor of lipoprotein-associated phospholipase A2. Bioorg Med Chem Lett 2003, 13, 6, 1067.
2 Ife, R.J.; Leach, C.A.; Hickey, D.M.B.; Pinto, I.L.; Smith, S.A.; Stanway, S.J. (GlaxoSmithKline plc); Pyrimidine-4-one derivs. as LDL-PLA 2 inhibitors. EP 1263740; JP 2003523335; US 2002103213; US 6649619; WO 0160805 .
3 Mulholland, K.R.; Ross, A.R.; Smith, G.E.; Slater, G.R. (GlaxoSmithKline plc); Novel processes. WO 0316287 .
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) 29947 ethyl 2-oxocyclopentanecarboxylate 611-10-9 C8H12O3 详情 详情
(II) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(III) 63490 2-sulfanyl-3,5,6,7-tetrahydro-4H-cyclopenta[d]pyrimidin-4-one C7H8N2OS 详情 详情
(IV) 12354 4-Fluorobenzyl chloride; 1-(Chloromethyl)-4-fluorobenzene 352-11-4 C7H6ClF 详情 详情
(V) 63491 2-{[(4-fluorophenyl)methyl]sulfanyl}-3,5,6,7-tetrahydro-4H-cyclopenta[d]pyrimidin-4-one C14H13FN2OS 详情 详情
(VI) 24735 tert-Butyl 2-iodoacetate C6H11IO2 详情 详情
(VII) 63492 1,1-dimethylethyl 2-(2-{[(4-fluorophenyl)methyl]sulfanyl}-4-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-1-yl)acetate C20H23FN2O3S 详情 详情
(VIII) 63494 2-(2-{[(4-fluorophenyl)methyl]sulfanyl}-4-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-1-yl)acetic acid C16H15FN2O3S 详情 详情
(IX) 63493 methyl 2-{[(trifluoromethyl)sulfonyl]oxy}acetate C4H5F3O5S 详情 详情
(X) 63495 methyl 2-(2-{[(4-fluorophenyl)methyl]sulfanyl}-4-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-1-yl)acetate C17H17FN2O3S 详情 详情
Extended Information