Methyl iodide → HCID 90229525, compound

HRID 1505799Notes

Reaction equation

HRID 1505799 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:5]([CH3:42])=[C:6]([NH:10][C:11]([C:13]2[C:21]3[N:20]=[C:19]([NH:22][CH2:23][C:24]([CH3:28])([CH3:27])[CH2:25][OH:26])[NH:18][C:17]=3[CH:16]=[C:15]([NH:29][C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:38]([F:41])([F:40])[F:39])=[O:31])[CH:14]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1.[CH3:43]I>CN(C=O)C.C(OCC)(=O)C>[Cl:3][C:4]1[C:5]([CH3:42])=[C:6]([NH:10][C:11]([C:13]2[C:21]3[N:20]=[C:19]([NH:22][CH2:23][C:24]([CH3:28])([CH3:27])[CH2:25][OH:26])[N:18]([CH3:43])[C:17]=3[CH:16]=[C:15]([NH:29][C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:38]([F:39])([F:40])[F:41])=[O:31])[CH:14]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 71267440HCID 71267440, compound

Product 1

HCID 90229525HCID 90229525, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydroxide powder (6.2 mg) was added to a solution of N-(3-chloro-2-methylphenyl)-2-[(3-hydroxy-2,2-dimethylpropyl)amino]-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (80 mg) in DMF (2 mL), the solution was stirred at room temperature for 30 minutes, methyl iodide (8.7 μL) was added, and it was stirred for 17 hours. The reaction mixture was diluted with ethyl acetate, washed with brine, and concentrated under reduced pressure. The residue was purified on column chromatography to obtain N-(3-chloro-2-methylphenyl)-2-[(3-hydroxy-2,2-dimethylpropyl)amino]-1-methyl-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (20 mg) as white powder. This was suspended in MeOH, 2N hydrogen chloride/EtOH (1 Eq) was added, it was stirred to obtain a solution, and the solvent was removed under reduced pressure. The residue was washed with diethyl ether, and the precipitate was collected by filtration and dried to obtain the titled compound (15 mg) as white powder.

Workup

  1. stirringit was stirred for 17 hours
  2. washwashed with brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-842096dccb3041c5a3f8c0489c1dcb57
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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