Potassium Carbonate → HCID 22327405, compound

HRID 495663Notes

Reaction equation

[CH2:1]([N:3]([CH2:22][CH3:23])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([C:19]#[N:20])[CH:13]=[C:14]([C:15]([F:18])([F:17])[F:16])[C:9]=2[NH:8][C:7]1=[O:21])[CH3:2].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH2:28]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:22]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([C:19]#[N:20])[CH:13]=[C:14]([C:15]([F:16])([F:17])[F:18])[C:9]=2[N:8]([CH2:28][C:27]2[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=2[C:25]([F:24])([F:34])[F:35])[C:7]1=[O:21])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-[2-(diethylamino)ethyl]-2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-5-carbonitrile (19.1 mg), 2-trifluoromethylbenzyl bromide (30.4 mg) and potassium carbonate (16.5 mg) in N,N-dimethylformamide (3 ml) was stirred with heating at 80° C. for 1.5 hours. To the mixture was further added 2-trifluoromethylbenzyl bromide (46.8 mg), and the mixture was stirred with heating at 80° C. for 1 hour. 2-Trifluoromethylbenzyl bromide (160.3 mg) and potassium carbonate (43.2 mg) were further added, and the mixture was stirred with heating 80° C. for 1 hour. The reaction mixture was concentrated in vacuo. The resultant residue was purified by preparative TLC (1 mm, 20×20 cm, chloroform:methanol=25:1) to give the title compound (2.8 mg, 10%).

Workup

stirringthe mixture was stirred
temperaturewith heating at 80° C. for 1 hour
stirringthe mixture was stirred
temperaturewith heating 80° C. for 1 hour
concentrationThe reaction mixture was concentrated in vacuo
customThe resultant residue was purified by preparative TLC (1 mm, 20×20 cm, chloroform:methanol=25:1)

Sources & evidence

ORD record: ord-1c4fa90da9134658acf0d6d797af7789
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939887B2

Reaction notes

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