Dimethylformamide → HCID 18464882、化合物

HRID 1584501ノート

反応式

HRID 1584501 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].CN(C)C=O.[H-].[Na+].[CH3:31][O:32][CH2:33][CH2:34]Cl>ClCCl.ClCCl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]([CH2:34][CH2:33][O:32][CH3:31])[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

7

反応物 4

HCID 6228DimethylformamideHCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 184646551-t-butoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane

生成物 1

HCID 18464882HCID 18464882、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
85 °C

実験手順

Combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepane (2.03 g, 6.41 mmol) and dimethylformamide (50 mL). Cool in an ice-bath. Add sodium hydride (0.28 g, 60% in oil, 7.0 mmol). After 20 minutes, add 2-chloroethyl methyl ether (0.7 mL, 7.66 mmol). Heat to 85° C. After 18 hours, cool to ambient temperature and dilute with dichloromethane, and extract with water, a saturated aqueous sodium bicarbonate solution, and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with dichloromethane/methanol/concentrated ammonium hydroxide 95/5/0.05 to give 1-(t-butoxycarbonyl)-4-(1-(2-methoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane.

後処理

  1. temperatureCool in an ice-bath
  2. waitAfter 18 hours
  3. temperaturecool to ambient temperature
  4. extractionextract with water
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue

出典と根拠

ORDレコード
ord-007355bcb8584888acf307dd50683d4b
出典データセット
uspto-grants-1999_08
特許番号
US05932571

反応ノート

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