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

HRID 1255848Notes

Reaction equation

HRID 1255848 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]=1

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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

  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)

Sources & evidence

ORD record
ord-e0990ef3656243928b8df7e0e22f9159
Source dataset
uspto-grants-2013_06
Patent number
US08461161B2

Reaction notes

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