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Ethyl Acetate → N-(5-(7-Chloro-3-(2-chlorobenzyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)pyridin-2-yl)acetamide

HRID 1910693
ノート
印刷プレビュー

反応式

HRID 1910693 の反応式
[Cl:1][C:2]1[CH:40]=[CH:39][C:5]2[N:6](CC3C=CC(OC)=CC=3)[C:7](=[O:29])[CH:8]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[N:15][CH:16]=3)[C:4]=2[CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].C(OCC)(=O)C>C1(OC)C=CC=CC=1>[Cl:1][C:2]1[CH:40]=[CH:39][C:5]2[NH:6][C:7](=[O:29])[CH:8]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[N:15][CH:16]=3)[C:4]=2[CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8857Ethyl Acetate2 回HCID 6451240Aluminum(III) ChlorideHCID 67283418N-(5-(7-Chloro-3-(2-chlorobenzyl)-1-(4-methoxybenzyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)pyridin-2-yl)acetamide

生成物 1

HCID 67282623N-(5-(7-Chloro-3-(2-chlorobenzyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)pyridin-2-yl)acetamide収率 72.3%

試薬・触媒・溶媒 1

HCID 7519
Anisole
溶媒

反応条件

温度
85 °C

実験手順

N-(5-(7-Chloro-3-(2-chlorobenzyl)-1-(4-methoxybenzyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)pyridin-2-yl)acetamide (210 mg, 0.366 mmol) was dissolved in anisole (1 mL) under nitrogen and AlCl3 (195 mg, 1.465 mmol) was added in one portion. The resulting orange solution was heated to 85° C. for 2 h then allowed to cool. Ice and ethyl acetate were added and the mixture was stirred for 30 min then partitioned and the organic layer was washed with water then brine and dried (MgSO4). Chromatography on silica gel eluting with 10%-50%-70% ethyl acetate in hexanes gave the product (120 mg, 72% yield). 1H-NMR (300 MHz, CDCl3) δ 7.62-7.5 (m, 3H), 7.5-7.20 (m, 7H), 6.49 (s, 1H), 6.47 (s, 1H), 4.31 (dd, 1H), 4.25-4.17 (m, 2H), 3.59 (dd, 1H), 3.35 (dd, 1H). HRMS (ES+) m/z calcd for C23H18Cl2N4O2 [M+H]+, 453.0885. found, 453.0872.

後処理

  1. temperatureto cool
  2. customthen partitioned
  3. washthe organic layer was washed with water
  4. dry with materialbrine and dried (MgSO4)

出典と根拠

ORDレコード
ord-8729b24f764c4799a5a878bae4a09fd0
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08604023B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート