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Sodium hydride → N-(1-Cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-2-(hex-5-enyl-methyl-amino-carbonyl)-4-(2-chloropyrimidin-4-yloxy)-cyclopentane-carboxamide

HRID 1429156
ノート
印刷プレビュー

反応式

HRID 1429156 の反応式
[CH:1]1([S:4]([NH:7][C:8]([C:10]2([NH:15][C:16]([CH:18]3[CH2:22][CH:21]([OH:23])[CH2:20][CH:19]3[C:24]([N:26]([CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[CH3:27])=[O:25])=[O:17])[CH2:12][CH:11]2[CH:13]=[CH2:14])=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[H-].[Na+].[Cl:36][C:37]1[N:42]=[C:41](Cl)[CH:40]=[CH:39][N:38]=1>CN(C=O)C>[CH:1]1([S:4]([NH:7][C:8]([C:10]2([NH:15][C:16]([CH:18]3[CH2:22][CH:21]([O:23][C:39]4[CH:40]=[CH:41][N:42]=[C:37]([Cl:36])[N:38]=4)[CH2:20][CH:19]3[C:24]([N:26]([CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[CH3:27])=[O:25])=[O:17])[CH2:12][CH:11]2[CH:13]=[CH2:14])=[O:9])(=[O:6])=[O:5])[CH2:2][CH2:3]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 24758Sodium hydrideHCID 775312,4-DichloropyrimidineHCID 68589808N-(1-Cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-2-(hex-5-enyl-methyl-amino-carbonyl)-4-hydroxy-cyclopentane-carboxamide

生成物 1

HCID 72253694N-(1-Cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-2-(hex-5-enyl-methyl-amino-carbonyl)-4-(2-chloropyrimidin-4-yloxy)-cyclopentane-carboxamide収率 81%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Compound 10e (43 mg, 89.3 mmol) was dissolved in DMF (2 ml) and the solution was cooled to 0° C. and NaH (11 mg, 0.27 mmol) was added. After 0.5 h 2,4-dichloro-pyrimidine was added. The reaction was stirred at 0° C. for 2 h and then quenched by addition of citric acid. The reaction mixture was extracted with DCM (3×10 ml) and the combined organic phases were washed with citric acid, water and brine. The organic phase was dried over MgSO4 and filtered. The solvent was removed in vacuo to yield the crude target compound (43 mg, 81%); LC/MS m/z (ESI+)=595 (MH+).

後処理

  1. customquenched by addition of citric acid
  2. extractionThe reaction mixture was extracted with DCM (3×10 ml)
  3. washthe combined organic phases were washed with citric acid, water and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-5145844a747c47c88d289c92704d2f7d
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08937080B2

反応ノート

読み込み中…

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