Potassium Carbonate → HCID 10202173, compound

HRID 276063Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[C:9]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[C:22]([CH2:25]Cl)[CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[CH3:27])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:9]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[C:22]([CH2:25][NH:1][CH2:2][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=4)[CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[CH3:27])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-Aminomethylpyridine (0.372 g) was added to a solution of 0.597 g of 1-(biphenyl-4-ylmethyl)-6-chloromethyl-2-methylbenzimidazole and 0.350 g of potassium carbonate in 3 ml of N,N-dimethylformamide, and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was extracted with water and with ethyl acetate. The organic layer was washed twice with water, and the solvent was distilled off under reduced pressure. The resulting residue was purified through silica-gel column chromatography (eluent: a mixture of chloroform and methanol at a ratio of 9:1), and was recrystallized from a mixed solvent of ethyl acetate and hexane to give 0.300 g of 1-(biphenyl-4-ylmethyl)-2-methyl-6-[2-pyridylmethyl)aminomethyl]benzimidazole (265).

Workup

extractionThe reaction mixture was extracted with water and with ethyl acetate
washThe organic layer was washed twice with water
distillationthe solvent was distilled off under reduced pressure
customThe resulting residue was purified through silica-gel column chromatography (eluent
additiona mixture of chloroform and methanol at a ratio of 9:1), and
customwas recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record: ord-6df8a6ef1b984043a8d669e43808008f
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352985B1

Reaction notes

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