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【结 构 式】

【分子编号】36719

【品名】3,3-diphenylpropanamide

【CA登记号】

【 分 子 式 】C15H15NO

【 分 子 量 】225.29024

【元素组成】C 79.97% H 6.71% N 6.22% O 7.1%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(III)

3,3-Diphenylpropionic acid (I) was treated with SOCl2 to give acid chloride (II) and then converted to amide (III) using liquid ammonia. Dehydration with P2O5 led to diphenylpropionitrile (IV), which was treated with SOCl2 in methanol to afford the iminoester (V). The condensation of (V) wiith 2-oxobutan-1,4-diol (VI) in liquid ammonia furnished imidazole (VII). Further treatment of (VII) with SOCl2 provided chloride (VIII). Finally, reaction of (VIII) with methylamine in the presence of K2CO3 and a catalytic amount of KI afforded the title compound.

1 Schunack, W.; Detert, H.; Pertz, H.H.; Kramer, K.; ter Laak, A.M.; Kühne, RF.; Elz, S.; Histaprofidens: Synthesis, pharmacological in vitro evaluation, and molecular modeling of a new class of highly active and selective histamine H1-receptor agonists. J Med Chem 2000, 43, 6, 1071.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
11021 Methanamine; Methylamine 74-89-5 CH5N 详情 详情
(I) 36717 3,3-diphenylpropionic acid 606-83-7 C15H14O2 详情 详情
(II) 36718 3,3-diphenylpropanoyl chloride C15H13ClO 详情 详情
(III) 36719 3,3-diphenylpropanamide C15H15NO 详情 详情
(IV) 36720 3,3-diphenylpropanenitrile 2286-54-6 C15H13N 详情 详情
(V) 36721 methyl 3,3-diphenylpropanimidoate C16H17NO 详情 详情
(VI) 36722 1,4-dihydroxy-2-butanone C4H8O3 详情 详情
(VII) 36723 2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]-1-ethanol C20H22N2O 详情 详情
(VIII) 36724 4-(2-chloroethyl)-2-(3,3-diphenylpropyl)-1H-imidazole C20H21ClN2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

3,3-Diphenylpropionic acid (I) was treated with SOCl2 to give acid chloride (II) and then converted to amide (III) using liquid ammonia. Dehydration of (III) with P2O5 led to diphenylpropionitrile (IV), which was treated with ammonia in methanol to afford the iminoester (V). The condensation of (V) with 2-oxo-4-phthalimido-1-butyl acetate (VI) in liquid ammonia furnished imidazole (VII). Finally, deprotection of the phthaloyl group of (VII) with methanolic hydrazine afforded the title compound.

1 Schunack, W.; Detert, H.; Pertz, H.H.; Kramer, K.; ter Laak, A.M.; Kühne, RF.; Elz, S.; Histaprofidens: Synthesis, pharmacological in vitro evaluation, and molecular modeling of a new class of highly active and selective histamine H1-receptor agonists. J Med Chem 2000, 43, 6, 1071.
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) 36717 3,3-diphenylpropionic acid 606-83-7 C15H14O2 详情 详情
(II) 36718 3,3-diphenylpropanoyl chloride C15H13ClO 详情 详情
(III) 36719 3,3-diphenylpropanamide C15H15NO 详情 详情
(IV) 36720 3,3-diphenylpropanenitrile 2286-54-6 C15H13N 详情 详情
(V) 36721 methyl 3,3-diphenylpropanimidoate C16H17NO 详情 详情
(VI) 36725 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-oxobutyl acetate C14H13NO5 详情 详情
(VII) 36726 2-[2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethyl]-1H-isoindole-1,3(2H)-dione C28H25N3O2 详情 详情
Extended Information