4-amino-N-methylbenzamide -Drug Synthesis Database

【结构式】

【分子编号】67862

【品名】4-amino-N-methylbenzamide

【CA登记号】6274-22-2

【分子式】C₈H₁₀N₂O

【分子量】150.18028

【元素组成】C 63.98% H 6.71% N 18.65% O 10.65%

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：(VI)

Condensation of 3-chloropyrazine-2-carbonitrile (I) with N-methylmethanesulfonamide (II) in the presence of Cs2CO3 in acetonitrile at 80 °C gives N-(3-cyano-2-pyrazinyl)-N-methylmethanesulfonamide (III), which by nitrile reduction using H2 over Pd/C in methanolic ammonia, followed by treatment with AcOH in EtOAc provides the primary amine (IV). Condensation of 2,4-dichloro-5-(trifluoromethyl) pyrimidine (V) with 4-amino-N-methylbenzamide (VI) by means of ZnBr2 and Et3N in DCE/t-BuOH affords diaryl amine (VII). Finally, (aminomethyl)pyrazine (IV) is coupled with chloropyrimidine (VII) in the presence of DIEA in DCE/t-BuOH at 80 °C and the resulting free base is treated with HCl in MeOH .

参考文献中间体

合成目标

【1】 Luzzio, M.J., Autry, C.L., Bhattacharya, S.K. et al. (Pfizer Products Inc. ). Sulfonyl amide derivatives for the treatment of abnormal cell growth. US 2014100368; US 8247411; EP 2146779; US 2013005964; JP 2010524914; CN 103951658; US 2011166120; US 8440822; WO 2008129380.

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)	42535	3-chloro-2-pyrazinecarbonitrile	55557-52-3	C₅H₂ClN₃	详情	详情
(II)	67859	N-methylmethanesulfonamide	1184-85-6	C₂H₇NO₂S	详情	详情
(III)	67860	N-(3-cyano-2-pyrazinyl)-N-methylmethanesulfonamide		C₇H₈N₄O₂S	详情	详情
(IV)	67861	N-(3-(aminomethyl)pyrazin-2-yl)-N-methylmethanesulfonamide acetate		C₇H₁₂N₄O₂S.C₂H₄O₂	详情	详情
(V)	67477	2,4-dichloro-5-(trifluoromethyl)pyrimidine	3932-97-6	C₅HCl₂F₃N₂	详情	详情
(VI)	67862	4-amino-N-methylbenzamide	6274-22-2	C₈H₁₀N₂O	详情	详情
(VII)	67863	4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)-N-methylbenzamide		C₁₃H₁₀ClF₃N₄O	详情	详情
(VIII)	67864	N-methyl-4-((4-(((3-(N-methylmethylsulfonamido)pyrazin-2-yl)methyl)amino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzamide		C₂₀H₂₁F₃N₈O₃S	详情	详情

Extended Information