Pyridine → HCID 71267448, compound

HRID 1505784Notes

Reaction equation

HRID 1505784 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:5]([CH3:40])=[C:6]([NH:10][C:11]([C:13]2[C:21]3[N:20]=[C:19]([C@@H:22]4[CH2:26][CH2:25][CH2:24][NH:23]4)[NH:18][C:17]=3[CH:16]=[C:15]([NH:27][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]([F:39])([F:38])[F:37])=[O:29])[CH:14]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1.N1C=CC=CC=1.[C:47](Cl)(=[O:49])[CH3:48]>C1COCC1>[C:47]([N:23]1[CH2:24][CH2:25][CH2:26][C@H:22]1[C:19]1[NH:18][C:17]2[CH:16]=[C:15]([NH:27][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]([F:39])([F:37])[F:38])=[O:29])[CH:14]=[C:13]([C:11]([NH:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[C:5]=3[CH3:40])=[O:12])[C:21]=2[N:20]=1)(=[O:49])[CH3:48]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 90229289HCID 90229289, compound

Product 1

HCID 71267448HCID 71267448, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3-chloro-2-methylphenyl)-2-[(2S)-pyrrolidin-2-yl]-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (Example 71) (26 mg) in THF solution (0.5 mL), was added pyridine (12 μL), and the mixture was stirred under ice-cooling. To the mixture was added acetyl chloride (5.1 μL), and it was stirred at room temperature for 1 hour. To the reaction mixture was added ice water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified on column chromatography to obtain the titled compound (15 mg) as white powder.

Workup

  1. temperaturecooling
  2. stirringwas stirred at room temperature for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-0b7278d95004457cb63816da8bfffd2f
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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