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【结 构 式】

【分子编号】41663

【品名】N-[4-(2-chloroacetyl)phenyl]acetamide

【CA登记号】

【 分 子 式 】C10H10ClNO2

【 分 子 量 】211.64764

【元素组成】C 56.75% H 4.76% Cl 16.75% N 6.62% O 15.12%

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:(X)

The reduction of the ester function of (I) with LiAlH4 in THF gives (II). O-demethylation of (II) with EtSNa in DMF yields alcohol (III), which is then cyclized by Mitsunobu reaction with DEAD·Ph3P in THF to yield (IV). Displacement of the Br of (IV) by means of Zn(CN)2 and Pd(PPh3)4 in DMF affords cyano derivative (V), which is then converted into (VI) after debenzylation by treatment with HCl/EtOH and H2 over Pd/C. Finally (VI) is coupled with aldehyde (VII) by reductive amination in 1,2-dichloroethane in presence of NaBH(OAc)3.Alternatively the final product can be obtained by reaction of (VI) with chloro derivative (X) in CH3CN in presence of K2CO3 and KI. (X) can be obtained by acylation of acetanilide (VIII) with chloride (A) in 1,2-dichloroethane in presence of AlCl3 followed by treatment with TFA and Et3SiH.

1 Audinot, V.; Dubuffet, T.; Newman-Tancredi, A.; Cussac, D.; Millan, M.J.; Lavielle, G.; Loutz, A.; Novel benzopyrano[3,4-c]pyrrole derivatives as potent and selective dopamine D3 receptor antagonists. Bioorg Med Chem Lett 1999, 9, 14, 2059.
2 Lejeune, F.; Hautefaye, P.; Millan, M.; Dubuffet, T.; Lavielle, G. (ADIR et Cie.); Chromene derivs., process for their preparation and pharmaceutical compsns. containing them. EP 0887350; JP 1999071376; US 6090837 .
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) 33760 methyl (3R,4S)-1-benzyl-4-(5-bromo-2-methoxyphenyl)-3-pyrrolidinecarboxylate C20H22BrNO3 详情 详情
(II) 33761 [(3R,4S)-1-benzyl-4-(5-bromo-2-methoxyphenyl)pyrrolidinyl]methanol C19H22BrNO2 详情 详情
(III) 33762 2-[(3S,4R)-1-benzyl-4-(hydroxymethyl)pyrrolidinyl]-4-bromophenol C18H20BrNO2 详情 详情
(IV) 41665 (3aS,9bR)-2-benzyl-8-bromo-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole C18H18BrNO 详情 详情
(V) 41666 (3aS,9bR)-2-benzyl-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole-8-carbonitrile C19H18N2O 详情 详情
(VI) 41667 (3aS,9bR)-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole-8-carbonitrile C12H12N2O 详情 详情
(VII) 41662 N-[4-(2-oxoethyl)phenyl]acetamide C10H11NO2 详情 详情
(VIII) 10194 N-Phenylacetamide; Acetanilide 103-84-4 C8H9NO 详情 详情
(IX) 11296 2-Chloroacetyl chloride; Chloroacetic chloride 79-04-9 C2H2Cl2O 详情 详情
(X) 41663 N-[4-(2-chloroacetyl)phenyl]acetamide C10H10ClNO2 详情 详情
(XI) 41664 N-[4-(2-chloroethyl)phenyl]acetamide C10H12ClNO 详情 详情
Extended Information