Water → HCID 10309244, compound

HRID 1357038Notes

Reaction equation

HRID 1357038 reaction equation
[N:1]1([C:7]2[NH:8][C:9]3[CH:15]=[C:14]([C:16]([NH2:18])=[O:17])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[F:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:28]=1[CH2:29]Br.O>CN(C=O)C>[F:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:28]=1[CH2:29][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[NH:8][C:9]3[CH:15]=[C:14]([C:16]([NH2:18])=[O:17])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 54500560HCID 54500560, compound

Product 1

HCID 10309244HCID 10309244, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Piperazinyl-benzimidazole-5-carboxamide (0.186 g, 0.5 mMol) was taken in 5 mL DMF and 0.101 g (1 mMol) triethylamine was added and stirred for 15 minutes at room temperature. To this reaction mixture was added 0.104 g 2,6-difluorobenzyl bromide and the mixture was stirred for 20 h. This was poured into water and extracted with methylene chloride (3×50 mL). The combined extract was further washed with brine, water and dried over MgSO4. The solvent was removed in vacuo and the residue chromatographed on silica gel eluting with chloroform-methanol (0 to 5% methanol, gradient). Evaporation of the desired fraction gave 48.9 mg of the desired product; MS(ESI) m/e 356 (M+).

Workup

  1. stirringthe mixture was stirred for 20 h
  2. extractionextracted with methylene chloride (3×50 mL)
  3. extractionThe combined extract
  4. washwas further washed with brine, water
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customthe residue chromatographed on silica gel eluting with chloroform-methanol (0 to 5% methanol, gradient)
  8. customEvaporation of the desired fraction

Sources & evidence

ORD record
ord-c6f0955ed94841b19e6f2e29e894070c
Source dataset
uspto-grants-2003_07
Patent number
US06589954B1

Reaction notes

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