Potassium Carbonate → HCID 22327398, compound

HRID 495665Notes

Reaction equation

HRID 495665 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][C:29]([CH2:30]Br)=[CH:28][CH:27]=1.[C:36](=[O:39])([O-])[O-:37].[K+].[K+]>CN(C)C=O>[F:16][C:15]([F:18])([F:17])[C:36]([OH:37])=[O:39].[CH2:22]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([C:19]([NH2:20])=[O:37])[CH:13]=[C:14]([C:15]([F:16])([F:17])[F:18])[C:9]=2[N:8]([CH2:30][C:29]2[CH:32]=[CH:33][C:26]([C:25]([F:35])([F:34])[F:24])=[CH:27][CH:28]=2)[C:7]1=[O:21])[CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 22327412HCID 22327412, compound

Product 1

HCID 22327398HCID 22327398, compoundYield 166%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-[2-(diethylamino)ethyl]-2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-5-carbonitrile (12.5 mg), 4-trifluoromethylbenzyl bromide (24.9 mg) and potassium carbonate (12.9 mg) in N,N-dimethylformamide (1.5 ml) was stirred with heating at 80° C. for 1.5 hours. The reaction mixture was concentrated in vacuo. To the resultant residue was added t-butanol (3 ml), and the mixture was stirred with heating at 60° C. To the solution was added powdered potassium hydroxide crashed in mortar (47.9 mg), and the mixture was stirred with heating at 60° C. for 45 minutes. To the reaction mixture was added 1N hydrochloric acid, and the mixture was concentrated in vacuo. The resultant residue was purified by HPLC using condition 2 to give the title compound (19.6 mg, 83%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionTo the resultant residue was added t-butanol (3 ml)
  3. temperaturewith heating at 60° C
  4. additionTo the solution was added
  5. stirringthe mixture was stirred
  6. temperaturewith heating at 60° C. for 45 minutes
  7. additionTo the reaction mixture was added 1N hydrochloric acid
  8. concentrationthe mixture was concentrated in vacuo
  9. customThe resultant residue was purified by HPLC

Sources & evidence

ORD record
ord-a9f9d273c2214c8a9df297cf0b360dfe
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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