Triethylamine → (S)-N-(3-(1-(6-chloropyrazin-2-ylamino)ethyl)phenyl)-1H-benzo[d]imidazole-6-carboxamide

HRID 572222

反応式

HRID 572222 の反応式
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](Cl)=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1.[NH2:13][C:14]1[CH:15]=[C:16]([C@@H:20]([NH:22][C:23]2[CH:28]=[N:27][CH:26]=[C:25]([Cl:29])[N:24]=2)[CH3:21])[CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C>C(OCC)(=O)C>[Cl:29][C:25]1[N:24]=[C:23]([NH:22][C@H:20]([C:16]2[CH:15]=[C:14]([NH:13][C:10]([C:8]3[CH:7]=[CH:6][C:5]4[N:1]=[CH:2][NH:3][C:4]=4[CH:9]=3)=[O:11])[CH:19]=[CH:18][CH:17]=2)[CH3:21])[CH:28]=[N:27][CH:26]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 151044571H-Benzimidazole-6-carbonyl chlorideHCID 25218447(S)-N-(1-(3-aminophenyl)ethyl)-6-chloropyrazin-2-amine

生成物 1

HCID 59331711(S)-N-(3-(1-(6-chloropyrazin-2-ylamino)ethyl)phenyl)-1H-benzo[d]imidazole-6-carboxamide

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 5-benzimidazole carbonyl chloride (108 mg, 0.5 mmol), (S)—N-(1-(3-aminophenyl)ethyl)-6-chloropyrazin-2-amine (144 mg, 0.5 mmol) and triethylamine (0.7 mL, 5 mmol) was stirred at room temperature for 72 hours. After this time the mixture was allowed to cool to room temperature and was diluted with ethyl acetate (20 mL), washed with saturated aqueous sodium hydrogen carbonate (2×15 mL), brine (15 mL), dried (MgSO4) and concentrated under reduced pressure to give a yellow oil which was purified by flash chromatography (silica, ethyl acetate/methanol) to give (S)—N-(3-(1-(6-chloropyrazin-2-ylamino)ethyl)phenyl)-1H-benzo[d]imidazole-6-carboxamide as a yellow powder.

後処理

  1. temperatureto cool to room temperature
  2. washwashed with saturated aqueous sodium hydrogen carbonate (2×15 mL), brine (15 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give a yellow oil which
  6. customwas purified by flash chromatography (silica, ethyl acetate/methanol)

出典と根拠

ORDレコード
ord-d16d85b003914e2bb864acffe75d7e12
出典データセット
uspto-grants-2015_05
特許番号
US09029386B2

関連ノート

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