Sodium hydride → 4-(1-cyclopropylmethyl-1H-benzoimidazol-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 2230708ノート

反応式

HRID 2230708 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:27][CH:28]1[CH2:30][CH2:29]1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]([CH2:27][CH:28]3[CH2:30][CH2:29]3)[C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 184646551-t-butoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane

生成物 1

HCID 701476134-(1-cyclopropylmethyl-1H-benzoimidazol-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester収率 121.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Treat a solution of 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepan (0.50 g, 1.58 mmol, Preparation 9) and dimethylformamide (10 mL) with sodium hydride (0.083 g, 2.08 mmol, 60% dispersion in oil) at room temperature. After 15 minutes, add (bromomethyl)cyclopropane (0.21 mL, 2.17 mmol, Aldrich Chemical Company) and heat two hours at 80° C. Cool the reaction and partition between dichloromethane (150 mL) and NaHCO3 solution (40 mL). Wash the organic phase with brine (40 mL), dry (MgSO4), filter and concentrate the filtrate to afford 4-(1-cyclopropylmethyl-1H-benzoimidazol-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.71 g, Rf=0.87, silica gel, 95:5:0.5 dichloromethane:methanol:ammonium hydroxide).

後処理

  1. temperatureCool
  2. customthe reaction
  3. custompartition between dichloromethane (150 mL) and NaHCO3 solution (40 mL)
  4. washWash the organic phase with brine (40 mL)
  5. dry with materialdry (MgSO4)
  6. filtrationfilter
  7. concentrationconcentrate the filtrate

出典と根拠

ORDレコード
ord-2f9590001cea458e984284c9bef64bc9
出典データセット
uspto-grants-2002_07
特許番号
US06423704B1

反応ノート

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