N-Methyl-N-[(3RS,4RS)-4-methyl-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine -Drug Synthesis Database

【结构式】

【分子编号】65393

【品名】N-Methyl-N-[(3RS,4RS)-4-methyl-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

【CA登记号】　

【分子式】C₁₃H₁₉N₅

【分子量】245.32756

【元素组成】C 63.65% H 7.81% N 28.55%

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：(V)

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.

参考文献中间体

合成目标

【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