Dimethylformamide → HCID 10202173, compound

HRID 840776Notes

Reaction equation

HRID 840776 reaction equation
CN(C)C=O.[C:6]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:17]3[CH:18]=[C:19]([CH2:22]Cl)[CH:20]=[CH:21][C:16]=3[N:15]=[C:14]2[CH3:24])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1>C(OCC)(=O)C.O>[C:6]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:17]3[CH:18]=[C:19]([CH2:22][NH:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=4)[CH:20]=[CH:21][C:16]=3[N:15]=[C:14]2[CH3:24])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 195092-PyridinemethanamineHCID 22620345HCID 22620345, compound

Product 1

HCID 10202173HCID 10202173, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To an N,N-dimethylformamide (3 ml) solution of 1-(biphenyl-4-ylmethyl)-6-chloromethyl-2-methylbenzimidazole (0.597 g) and potassium carbonate (0.350 g), 2-aminomethylpyridine (0.372 g) is added and the solution is stirred for two hours at 60° C. Water and ethyl acetate are added and extraction is performed. An organic layer is washed with water (twice). The solvent is removed under reduced pressure and a residue is obtained. The residue is purified through silica gel column chromatography (eluate: chloroform/methanol=9/1). Recrystallization is performed in a mixture solvent of ethyl acetate and hexane and thus, 1-(biphenyl4-ylmethyl)-2-methyl-6-[(2-pyridylmethyl) aminomethyl]benzimidazole 0.300 g is obtained. 1H-NMR (CDCl3, δ): 2.57 (3H, s), 3.91 (2H, s), 3.93 (2H, s), 5.35 (2H, s), 7.08-7.14 (3H, m), 7.23 (2H, d, J=7.3 Hz), 7.30-7.35 (2H, m) 7.41 (2H, t), 7.50-7.55 (4H, m), 7.57 (1H, dt, J=1.8 and 7.6 Hz), 7.68 (1H, d, J=8.1 Hz), 8.53 (1H, d, J=4.9 Hz).

Workup

  1. extractionextraction
  2. washAn organic layer is washed with water (twice)
  3. customThe solvent is removed under reduced pressure
  4. customa residue is obtained
  5. customThe residue is purified through silica gel column chromatography (eluate: chloroform/methanol=9/1)
  6. customRecrystallization

Sources & evidence

ORD record
ord-3e706a567fb84da3bcf575b902faa848
Source dataset
uspto-grants-2002_04
Patent number
US06369092B1

Reaction notes

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