Imidazole → 4-[4-(1H-imidazol-1-ylmethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone

HRID 2186145ノート

反応式

HRID 2186145 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[C:14](=[O:32])[CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[NH:39]1[CH:43]=[CH:42][N:41]=[CH:40]1>CN(C=O)C>[N:39]1([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([S:9]([N:12]3[CH2:17][CH2:16][N:15]([CH2:18][CH:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]4)[C:14](=[O:32])[CH2:13]3)(=[O:11])=[O:10])=[CH:5][CH:4]=2)[CH:43]=[CH:42][N:41]=[CH:40]1

参加物

5

反応物 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 234476104-[4-(Bromomethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone

生成物 1

HCID 234473054-[4-(1H-imidazol-1-ylmethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone収率 100.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 4-[4-(bromomethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone (430 mg), potassium carbonate (112 mg) and imidazole (83 mg) in DMF (15 ml) was stirred at 70° C. for 1 hour. The reaction solution was concentrated, and to the residue was added water. The mixture was extracted with ethyl acetate, washed with water, sodium bicarbonate solution and brine, dried and concentrated, and the residue was recrystallized from ethyl acetate/hexane to give colorless crystals of 4-[4-(1H-imidazol-1-ylmethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone (421 mg).

後処理

  1. concentrationThe reaction solution was concentrated
  2. additionto the residue was added water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with water, sodium bicarbonate solution and brine
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was recrystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-6a155bb5a56842c4bac152450eaf5d98
出典データセット
uspto-grants-2002_06
特許番号
US06403595B1

反応ノート

読み込み中…