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【结 构 式】 
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【分子编号】65390 【品名】1-benzyl-4-methylpiperidin-3-one 【CA登记号】 |
【 分 子 式 】C12H17NO 【 分 子 量 】191.27312 【元素组成】C 75.35% H 8.96% N 7.32% O 8.36% |
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：(I)Racemic CP-690550 can be obtained by the following method. Reductive amination of 1-benzyl-4-methylpiperidin-3-one (I) with methylamine and sodium triacetoxyborohydride in THF gives N-methyl-1-benzyl-4-methylpiperidin-3-amine (II), which is condensed with 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (III) by means of triethylamine in a sealed tube at 100 °C to yield the tertiary amine (IV). After deprotection of (IV) by catalytic hydrogenolysis over Pd(OH)2/C, the debenzylated piperidine (V) is acylated with cyanoacetyl chloride (VI) and pyridine in CH2Cl2 to provide the target compound (1). Scheme 1.
| 【1】 Blumenkopf, T.A., Flanagan, M.E., Munchhof, M.J. (Pfizer Products Inc.). Pyrrolo[2,3-d]pyrimidine cpds. EP 1235830, JP 2003516405, US 2001053782, US 6627754, WO 0142246. |
| 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) | 65390 | 1-benzyl-4-methylpiperidin-3-one | C12H17NO | 详情 | 详情 | |
| (II) | 65391 | 1-Benzyl-N,4-dimethylpiperidin-3-amine; (1-Benzyl-4-methylpiperidin-3-yl)methylamine | 384338-23-2 | C14H22N2 | 详情 | 详情 |
| (III) | 60046 | 4-chloro-7H-pyrrolo[2,3-d]pyrimidine；6-Chloro-7-deazapurine；4-chloropyrrolo[2,3-d]pyrimidine；4-Chloro-1H-pyrrolo[2,3-d]pyrimidine | 3680-69-1 | C6H4ClN3 | 详情 | 详情 |
| (IV) | 65392 | N-Methyl-N-[(3RS,4RS)-4-methyl-1-(phenylmethyl)-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine | C20H25N5 | 详情 | 详情 | |
| (V) | 65393 | N-Methyl-N-[(3RS,4RS)-4-methyl-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine | C13H19N5 | 详情 | 详情 | |
| (VI) | 65394 | cyanoacetyl chloride | C3H2ClNO | 详情 | 详情 |
Extended Information