Hydrochloric Acid → HCID 22327391, compound

HRID 495664Notes

Reaction equation

HRID 495664 reaction equation
[CH2:1]([N:3]([CH2:33][CH3:34])[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[N:8]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:30])[F:29])[C:7]1=[O:32])[CH3:2].[OH-:35].[K+].Cl.C([OH:42])(C)(C)C>>[F:16][C:15]([F:18])([F:17])[C:14]([OH:42])=[O:35].[CH2:33]([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:42])[CH:13]=[C:14]([C:15]([F:18])([F:17])[F:16])[C:9]=2[N:8]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:30])([F:31])[F:29])[C:7]1=[O:32])[CH3:34]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 22327405HCID 22327405, compound

Product 1

HCID 22327391HCID 22327391, compound

Conditions

Temperature
60 °C

Procedure

A solution of 3-[2-(diethylamino)ethyl]-2-oxo-7-(trifluoromethyl)-1-[2-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrile (2.8 mg) in t-butanol (2 ml) was stirred with heating at 60° C. To the solution was added powdered potassium hydroxide crashed in mortar (24.3 mg), and the mixture was stirred with heating at 60° C. for 30 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 (4.0 mg, quantitative yield).

Workup

  1. additionTo the solution was added
  2. temperaturewith heating at 60° C. for 30 minutes
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe resultant residue was purified by HPLC

Sources & evidence

ORD record
ord-3d43cbd64f324b45962edd23ae20d30b
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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