Dichloromethane → HCID 71267551, compound

HRID 1505779Notes

Reaction equation

HRID 1505779 reaction equation
C(OC([N:8]([CH2:10][C:11]1[NH:15][C:14]2[CH:16]=[C:17]([NH:23][C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])=[O:25])[CH:18]=[C:19]([C:20]([OH:22])=O)[C:13]=2[N:12]=1)[CH3:9])=O)(C)(C)C.[C:36](O)([C:38](F)(F)F)=O.[CH2:43]([Cl:45])Cl>>[Cl:45][C:43]1[C:36]([CH3:38])=[C:13]([NH:12][C:20]([C:19]2[C:13]3[N:12]=[C:11]([CH2:10][NH:8][CH3:9])[NH:15][C:14]=3[CH:16]=[C:17]([NH:23][C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:34])([F:33])[F:35])=[O:25])[CH:18]=2)=[O:22])[CH:14]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 90229281HCID 90229281, compound

Product 1

HCID 71267551HCID 71267551, compound

Procedure

2-{[(tert-Butoxycarbonyl)(methyl)amino]methyl}-N-(3-chloro-2-methylphenyl)-6-({[2-(trifluoromethyl)phenyl]carbon yl}amino)-1H-benzimidazole-4-carboxamide (9 mg) was obtained according to the procedure as described in Step 7 of Example 11, using 2-{[(tert-butoxycarbonyl)(methyl)amino]methyl}-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxylic acid instead of 2-(methoxymethyl)-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxylic acid. This was dissolved in methylene chloride (1 mL). To the residue was added TFA (0.5 mL) under ice-cooling, and it was stirred for 0.5 hour. To the reaction mixture were added ice and then saturated aqueous sodium bicarbonate, and it was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified on column chromatography to obtain N-(3-chloro-2-methylphenyl)-2-[(methylamino)methyl]-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (5 mg) as slightly yellow powder. This was dissolved in MeOH (0.5 mL), and treated with 1M hydrochloric acid (2 Eq), and concentrated to obtain the titled compound (5 mg) as slightly yellow powder.

Workup

  1. temperaturecooling
  2. additionTo the reaction mixture were added ice
  3. extractionsaturated aqueous sodium bicarbonate, and it was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-843df3338a9d460b869177536d5206e4
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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