Dimethylformamide → HCID 86656345, compound

HRID 1942462Notes

Reaction equation

HRID 1942462 reaction equation
[CH:1]([N:4]([C:18]([C:20]1[C:21]([C:40]([F:43])([F:42])[F:41])=[CH:22][C:23]2[O:28][C:27]([CH3:30])([CH3:29])[C:26](=[O:31])[N:25]([CH2:32][CH2:33][NH:34][C:35]([O:37][CH3:38])=[O:36])[C:24]=2[CH:39]=1)=[O:19])[C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)([CH3:3])[CH3:2].[H-].[Na+].[CH3:46]N(C)C=O.CI>O>[CH:1]([N:4]([C:18]([C:20]1[C:21]([C:40]([F:41])([F:42])[F:43])=[CH:22][C:23]2[O:28][C:27]([CH3:30])([CH3:29])[C:26](=[O:31])[N:25]([CH2:32][CH2:33][N:34]([C:35]([O:37][CH3:38])=[O:36])[CH3:46])[C:24]=2[CH:39]=1)=[O:19])[C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:6]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67331342HCID 67331342, compound

Product 1

HCID 86656345HCID 86656345, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To tert-butyl (3R)-3-(isopropyl{[4-{2-[(methoxycarbonyl)amino]ethyl}-2,2-dimethyl-3-oxo-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}amino)piperidine-1-carboxylate (110 mg) were added sodium hydride (9.3 mg) and N,N-dimethylformamide (9 ml) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. Then, to the mixture was added methyl iodide (0.02 ml), and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate solution. The obtained ethyl acetate solution was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) to give the title compound (110 mg) as a colorless liquid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate solution
  4. washThe obtained ethyl acetate solution was washed with water
  5. dry with materialan aqueous sodium chloride solution, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-70850cc0e7e34183baa352fdff1f74c2
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

Loading…