• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】56910

【品名】N-(1,3-benzodioxol-5-ylmethyl)acrylamide

【CA登记号】

【 分 子 式 】C11H11NO3

【 分 子 量 】205.21328

【元素组成】C 64.38% H 5.4% N 6.83% O 23.39%

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:(III)

The reaction of 1,3-benzodioxol-5-ylmethylamine (I) with acryloyl chloride (II) by means of TEA gives the acrylamide (III), which is reductocondensed with perhydroazepine (IV) by means of LiAlH4 or BH3/THF in THF to yield the secondary amine (V). Finally this compound is condensed with 5-chloro-3-(3,5-difluorophenyl)isoxazole (VI) by means of BuLi in diethyl ether to afford the target tertiary amine. The intermediate 5-chloro-3-(3,5-difluorophenyl)isoxazole (VI) has been obtained by two related ways: The condensation of 3.5-difluorobenzoyl chloride (VII) with malonic acid monoethyl ester (VIII) by means of BuLi gives 2-(3,5-difluorobenzoyl)acetic acid ethyl ester (IX), which is cyclized with hydroxylamine in HOAc to yield 3-(3,5-difluorophenyl)isoxazol-5-ol (X). Finally this compound is treated with POCl3 to afford the desired 5-chloro-3-(3,5-difluorophenyl)isoxazole (VI) intermediate. Alternatively, the reaction of 3,5-difluoroacetophenone (XI) with diethyl carbonate (XII) by means of NaH yields also the already reported intermediate 2-(3,5-difluorobenzoyl)acetic acid ethyl ester (IX)

1 Nantermet, P.G.; et al.; Discovery of a nonpeptide small molecule antagonist of the human platelet thrombin receptor (PAR-1). Bioorg Med Chem Lett 2002, 12, 3, 319.
2 Freidinger, R.M.; Selnick, H.G.; Connolly, T.; Barrow, J.C.; Nantermet, P.G. (Merck & Co., Inc.); Isoxazole thrombin receptor antagonists. GB 2356198 .
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) 33669 1,3-benzodioxol-5-ylmethylamine; 1,3-benzodioxol-5-ylmethanamine; 3,4-Methylendioxybenzylamine 2620-50-0 C8H9NO2 详情 详情
(II) 11577 Acryloyl chloride; Acrylyl chloride;2-Propenoyl chloride 814-68-6 C3H3ClO 详情 详情
(III) 56910 N-(1,3-benzodioxol-5-ylmethyl)acrylamide C11H11NO3 详情 详情
(IV) 18672 azepane 111-49-9 C6H13N 详情 详情
(V) 56911 3-(1-azepanyl)-N-(1,3-benzodioxol-5-ylmethyl)-1-propanamine; N-[3-(1-azepanyl)propyl]-N-(1,3-benzodioxol-5-ylmethyl)amine C17H26N2O2 详情 详情
(VI) 56912 5-chloro-3-(3,5-difluorophenyl)isoxazole C9H4ClF2NO 详情 详情
(VII) 56913 3,5-Difluorobenzoyl chloride 129714-97-2 C7H3ClF2O 详情 详情
(VIII) 15086 3-ethoxy-3-oxopropionic acid 1071-46-1 C5H8O4 详情 详情
(IX) 56914 ethyl 3-(3,5-difluorophenyl)-3-oxopropanoate C11H10F2O3 详情 详情
(X) 56915 3-(3,5-difluorophenyl)-5-isoxazolol C9H5F2NO2 详情 详情
(XI) 56916 3,5-Difluoroacetophenone 123577-99-1 C8H6F2O 详情 详情
(XII) 17470 diethyl carbonate; diethylcarbonate 105-58-8 C5H10O3 详情 详情
Extended Information