Reaction equation
[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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- temperatureto cool to room temperature
- washwashed with saturated aqueous sodium hydrogen carbonate (2×15 mL), brine (15 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated under reduced pressure
- customto give a yellow oil which
- customwas purified by flash chromatography (silica, ethyl acetate/methanol)
Sources & evidence
- ORD record
- ord-d16d85b003914e2bb864acffe75d7e12
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029386B2
Linked notes
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