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【结 构 式】

【分子编号】48246

【品名】N-benzyl-N,N-dipropyl-1-propanaminium chloride

【CA登记号】

【 分 子 式 】C16H28ClN

【 分 子 量 】269.85776

【元素组成】C 71.21% H 10.46% Cl 13.14% N 5.19%

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:(A)

Condensation of 3,4,5-trichloro nitrobenzene (I) with 4-chlorobenzeneacetonitrile (II) by means of NaOH and N,N,N-triethylbenzylammonium chloride in THF yields substituted nitrobenzeneacetonitrile (III), which is subjected to hydrogenation over Pt/C in MeOH in the presence of thiophene to provide aniline (IV). Treatment of (IV) with HCl, HOAc and NaNO2, followed by reaction with ethyl N-(2-cyanoacetyl) carbamate (V) in AcOEt, furnishes ethyl carbamate derivative (VI), which is then subjected to cyclization by means of KOAc in refluxing HOAc to yield perhydro-3,5-dioxo-1,2,4-triazine derivative (VII). Hydrolysis of the nitrile moiety of (VII) by treatment with HCl in refluxing HOAc gives carboxylic acid (VIII), which is finally decarboxylated by heating in 2-mercaptoacetic acid to provide the desired product.

1 Boeckx, G.M.; Sipido, V.; Raeymaekers, A.H.M. (Janssen Pharmaceutica NV); alpha-Aryl-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetonitriles. AU 8545664; EP 0170316; ES 8609284; ES 8705403; JP 1986043176; JP 1993017454; US 4631278 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 13297 Thiophene 110-02-1 C4H4S 详情 详情
(A) 48246 N-benzyl-N,N-dipropyl-1-propanaminium chloride C16H28ClN 详情 详情
(I) 48245 1,2,3-trichloro-5-nitrobenzene 20098-48-0 C6H2Cl3NO2 详情 详情
(II) 22871 2-(4-chlorophenyl)acetonitrile 140-53-4 C8H6ClN 详情 详情
(III) 48247 2-(4-chlorophenyl)-2-(2,6-dichloro-4-nitrophenyl)acetonitrile C14H7Cl3N2O2 详情 详情
(IV) 48248 2-(4-amino-2,6-dichlorophenyl)-2-(4-chlorophenyl)acetonitrile C14H9Cl3N2 详情 详情
(V) 48249 ethyl 2-cyanoacetylcarbamate C6H8N2O3 详情 详情
(VI) 48250 ethyl 2-cyano-2-((Z)-2-[3,5-dichloro-4-[(4-chlorophenyl)(cyano)methyl]phenyl]hydrazono)acetylcarbamate C20H14Cl3N5O3 详情 详情
(VII) 48251 2-[3,5-dichloro-4-[(4-chlorophenyl)(cyano)methyl]phenyl]-3,5-dioxo-1,2,4-triazinane-6-carbonitrile C18H10Cl3N5O2 详情 详情
(VIII) 48252 2-[3,5-dichloro-4-[(4-chlorophenyl)(cyano)methyl]phenyl]-3,5-dioxo-1,2,4-triazinane-6-carboxylic acid C18H11Cl3N4O4 详情 详情
(C) 12893 Ethanethioic S-acid C2H4OS 详情 详情
Extended Information