Cesium carbonate → 1-[6-[(1,1-Dimethylethyl)amino]-2-pyrazinyl]-1H-benzimidazol-6-amine

HRID 2192685Notes

Reaction equation

HRID 2192685 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.[C:11]([NH:15][C:16]1[CH:21]=[N:20][CH:19]=[C:18](Cl)[N:17]=1)([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:11]([NH:15][C:16]1[N:17]=[C:18]([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:19]=[N:20][CH:21]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 53410761HCID 53410761, compoundHCID 178507353HCID 178507353, compound

Product 1

HCID 597839241-[6-[(1,1-Dimethylethyl)amino]-2-pyrazinyl]-1H-benzimidazol-6-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1H-benzimidazol-5-amine (2.93 g, 22 mmol), N-(tert-butyl)-6-chloropyrazin-2-amine (3.71 g, 20=not) and cesium carbonate (9.12 g, 28 mmol) in DMF (20 mL) was heated under N2 for 48 h. Upon cooling to RT the mixture was filtered and the filtrate concentrated in vacuo. The residue was extracted with CHCl3 and the solvent removed under reduced pressure. The residue was chromatographed using CH2Cl2-MeOH (98:2-93:7) to give from the less polar fractions 1-[6-(tert-butylamino)pyrazin-2-yl]-1H-benzimidazol-6-amine (1.38 g):

Workup

  1. temperaturewas heated under N2 for 48 h
  2. filtrationwas filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. extractionThe residue was extracted with CHCl3
  5. customthe solvent removed under reduced pressure
  6. customThe residue was chromatographed

Sources & evidence

ORD record
ord-920c98bd9b064a07bb97fd20a722233f
Source dataset
uspto-grants-2012_12
Patent number
US08329737B2

Reaction notes

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