Cesium carbonate → 1-(6-chloropyrazin-2-yl)-1H-benzimidazol-6-amine

HRID 2192686Notes

Reaction equation

HRID 2192686 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[N:3]=[CH:2]1.[Cl:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14](Cl)[N:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.ClCCl.CO>[Cl:11][C:12]1[N:13]=[C:14]([N:3]2[C:4]3[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=3[N:1]=[CH:2]2)[CH:15]=[N:16][CH:17]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 785042,6-DichloropyrazineHCID 178507353HCID 178507353, compound

Product 1

HCID 582170941-(6-chloropyrazin-2-yl)-1H-benzimidazol-6-amineYield 27%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 1H-benzimidazol-5-amine (0.8 g, 6 mmol), 2,6-dichloropyrazine (0.9 g, 6.0 mmol) and cesium carbonate (2.73 g, 8.4 mmol) in DMF (6 mL) was heated under N2 for 6 h. Upon cooling to RT the mixture was diluted with dichloromethane-methanol (6:1, 30 mL) and filtered and the filtrate concentrated in vacuo. The residue was chromatographed using CH2Cl2-MeOH (98:2-94:6) to give from the less polar fractions 1-(6-chloropyrazin-2-yl)-1H-benzimidazol-6-amine (398 mg):

Workup

  1. temperaturewas heated under N2 for 6 h
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was chromatographed

Sources & evidence

ORD record
ord-9cc08fbad68740d68501e8b0b19786c9
Source dataset
uspto-grants-2012_12
Patent number
US08329737B2

Reaction notes

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