Potassium Carbonate → HCID 10202173, compound

HRID 1276924Notes

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-d4bb0913959a47f1a769537d7daf29a3
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166219

Reaction notes

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