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【结 构 式】

【分子编号】49204

【品名】(2-[4-(4-fluorophenyl)-5-[2-(methylsulfanyl)-4-pyrimidinyl]-1H-imidazol-2-yl]-5-methyl-1,3-dioxan-5-yl)(4-morpholinyl)methanone

【CA登记号】

【 分 子 式 】C24H26FN5O4S

【 分 子 量 】499.5661432

【元素组成】C 57.7% H 5.25% F 3.8% N 14.02% O 12.81% S 6.42%

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:(XI)

Condensation of 2,2-bis(hydroxymethyl)propionic acid (VIII) with morpholine (IX) in the presence of DCC and HOBt gave amide (X). The cyclic ketal (XI) was then obtained by acid-catalyzed condensation of imidazole aldehyde (VII) with diol (X) using azeotropic removal of water. Oxidation of the sulfide group of (XI) with meta-chloroperbenzoic acid furnished sulfone (XII). The methylsulfonyl group of (XII) was finally displaced with cyclopropylamine (XIII) to provide the title compound

1 Collis, A.J.; Wilsher, N.E.; Foster, M.L.; Redford, E.J.; McLay, I.M.; Page, K.M.; Maslen, C.; Halley, F.; Souness, J.E.; RPR203494 a pyrimidine analogue of the p38 inhibitor RPR200765A with an improved in vitro potency. Bioorg Med Chem Lett 2001, 11, 5, 693.
2 Halley, F.; Porter, B.; Bamborough, P.L.; Lewis, R.A.; Ratcliffe, A.J.; Wallace, P.A.; McLay, I.M.; McKenna, J.M.; Lythgoe, D.J.; Collis, A.J. (Rhone-Poulenc Rorer Ltd.); Imidazolyl-cyclic acetals. EP 0988301; WO 9856788 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 49201 4-(4-fluorophenyl)-5-[2-(methylsulfanyl)-4-pyrimidinyl]-1H-imidazole-2-carbaldehyde C15H11FN4OS 详情 详情
(VIII) 49202 3-hydroxy-2-(hydroxymethyl)-2-methylpropionic acid C5H10O4 详情 详情
(IX) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(X) 49203 3-hydroxy-2-(hydroxymethyl)-2-methyl-1-(4-morpholinyl)-1-propanone C9H17NO4 详情 详情
(XI) 49204 (2-[4-(4-fluorophenyl)-5-[2-(methylsulfanyl)-4-pyrimidinyl]-1H-imidazol-2-yl]-5-methyl-1,3-dioxan-5-yl)(4-morpholinyl)methanone C24H26FN5O4S 详情 详情
(XII) 49205 (2-[4-(4-fluorophenyl)-5-[2-(methylsulfonyl)-4-pyrimidinyl]-1H-imidazol-2-yl]-5-methyl-1,3-dioxan-5-yl)(4-morpholinyl)methanone C24H26FN5O6S 详情 详情
(XIII) 12263 Cyclopropylamine; Cyclopropanamine 765-30-0 C3H7N 详情 详情
Extended Information