Dimethylformamide → N-methylpyridine-2-carboxamide

HRID 13488Notes

Reaction equation

HRID 13488 reaction equation
N[C:2]1[CH:18]=[CH:17][C:5]2[N:6]=[C:7](NC3C=CC(Br)=CC=3)[NH:8][C:4]=2[CH:3]=1.[H-].[Na+].CN(C)C=[O:24]>>[N:6]1[CH:3]=[CH:2][CH:18]=[CH:17][C:5]=1[C:4]([NH:8][CH3:7])=[O:24]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 22040962HCID 22040962, compound

Product 1

HCID 12272691N-methylpyridine-2-carboxamide

Procedure

To a solution of ((5-aminobenzimidazol-2-yl)(4-bromophenylamine (1 eq) in N,N-dimethylformamide was added sodium hydride (2 eq) and the mixture was microwaved for 8 mins at 220° C. The reaction mixture was partitioned between ethyl acetate and water and the organic layer was dried with sodium sulfate and concentrated. Preparative chromatography yielded [4-({2-[(4-bromophenyl)amino}benzimidazol-5-yl}amino)(2-pyridyl-N-methylcarboxamide. MS: MH+=437.

Workup

  1. customthe mixture was microwaved for 8 mins at 220° C
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. dry with materialthe organic layer was dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c7a9d1d99c204588a1e625c78dd8232b
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Reaction notes

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