Cesium carbonate → 6-Chloro-1-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-1,4-dihydro-benzo[d][1,3]oxazin-2-one

HRID 1710670ノート

反応式

HRID 1710670 の反応式
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][CH3:19])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[Cl:20][C:21]1[CH:31]=[CH:30][C:24]2[NH:25][C:26](=[O:29])[O:27][CH2:28][C:23]=2[CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[Cl:20][C:21]1[CH:31]=[CH:30][C:24]2[N:25]([CH2:2][C:3]([N:5]3[CH2:10][CH2:9][N:8]([C:11]4[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][CH3:19])[CH:12]=4)[CH2:7][CH2:6]3)=[O:4])[C:26](=[O:29])[O:27][CH2:28][C:23]=2[CH:22]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 11194716HCID 11194716、化合物HCID 210711262-Chloro-1-(4-(4-chloro-3-methoxyphenyl)piperazin-1-yl)ethanone

生成物 1

HCID 160596956-Chloro-1-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-1,4-dihydro-benzo[d][1,3]oxazin-2-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A mixture of 2-chloro-1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-ethanone (303 mg, 1 mmol, 1 equiv), 6-chloro-1,4-dihydro-benzo[d][1,3]oxazin-2-one (72) (183 mg, 1 equiv), and Cs2CO3 (56 μL, 4 equiv) in 2 ml of DMF was stirred at 60° C. overnight. The reaction solution was then diluted with EtOAc (50 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated in vacuo. The resultant crude residue was purified by flash chromatography to give 6-chloro-1-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-1,4-dihydro-benzo[d][1,3]oxazin-2-one (73): MS (ES) [M+H]+ expected 450.1, found 450.1.

後処理

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe resultant crude residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-d75da2d6d88d4b9f81fb2ad9f6becb59
出典データセット
uspto-grants-2010_09
特許番号
US07790726B2

反応ノート

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