【结 构 式】 |
【分子编号】65391 【品名】1-Benzyl-N,4-dimethylpiperidin-3-amine; (1-Benzyl-4-methylpiperidin-3-yl)methylamine 【CA登记号】384338-23-2 |
【 分 子 式 】C14H22N2 【 分 子 量 】218.34216 【元素组成】C 77.01% H 10.16% N 12.83% |
合成路线1
该中间体在本合成路线中的序号:(II)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 |