Pyridine → HCID 66614307, compound

HRID 1256610Notes

Reaction equation

[CH2:1]([NH:3][C:4]1[C:5]([NH2:14])=[CH:6][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:9]=1)[CH3:2].Cl.[C:16](Cl)(=O)[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.N1C=CC=CC=1.CCN=C=NCCCN(C)C>O>[CH2:1]([N:3]1[C:4]2[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:13])[F:12])=[CH:6][C:5]=2[N:14]=[C:16]1[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1.0 g of N1-ethyl-4-trifluoromethylbenzene-1,2-diamine, 1.05 g of isonicotinoyl chloride hydrochloride and 15 ml of pyridine was stirred for 4 hours at 60° C. Then, 0.94 g of WSC was added, and the mixture was stirred for 8 hours at 80° C. The reaction mixture was cooled down to room temperature. Into the reaction mixture was poured water, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with water and saturated saline, then, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.65 g of 1-ethyl-2-(pyridin-4-yl)-5-trifluoromethyl-1H-benzimidazole (hereinafter, referred to as present active compound 221).

Workup

stirringthe mixture was stirred for 8 hours at 80° C
temperatureThe reaction mixture was cooled down to room temperature
extractionthe mixture was extracted twice with ethyl acetate
washThe organic layer was washed with water and saturated saline
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-51d0f57bf9584e75813f76dabd2a8f18
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461181B2

Reaction notes

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