Dimethylformamide → HCID 49872513, compound

HRID 244380Notes

Reaction equation

HRID 244380 reaction equation
Cl.[CH:2]([N:5]([C@@H:32]1[CH2:37][CH2:36][CH2:35][NH:34][CH2:33]1)[C:6]([C:8]1[C:9]([C:28]([F:31])([F:30])[F:29])=[CH:10][C:11]2[O:16][C:15]([CH3:18])([CH3:17])[C:14](=[O:19])[N:13]([CH2:20][CH2:21][NH:22][C:23](=[O:26])[CH2:24][CH3:25])[C:12]=2[CH:27]=1)=[O:7])([CH3:4])[CH3:3].[C:38](=[O:41])([O-:40])[O-:39].[K+].[K+].CN(C=O)C>O>[CH:2]([N:5]([C@@H:32]1[CH2:37][CH2:36][CH2:35][N:34]([CH2:6][C:8]2[O:41][C:38](=[O:40])[O:39][C:27]=2[CH3:12])[CH2:33]1)[C:6]([C:8]1[C:9]([C:28]([F:30])([F:29])[F:31])=[CH:10][C:11]2[O:16][C:15]([CH3:17])([CH3:18])[C:14](=[O:19])[N:13]([CH2:20][CH2:21][NH:22][C:23](=[O:26])[CH2:24][CH3:25])[C:12]=2[CH:27]=1)=[O:7])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 67511771HCID 67511771, compound

Product 1

HCID 49872513HCID 49872513, compoundYield 147.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To N-isopropyl-2,2-dimethyl-3-oxo-N-[(3R)-piperidin-3-yl]-4-[2-(propionylamino)-ethyl]-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazine-6-carboxamide hydrochloride (1.0 g) were added the compound of Reference Example 8 (344 mg), potassium carbonate (45 mg) and DMF (30 ml), and the mixture was stirred at room temperature overnight. After the reaction was completed, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate solution was washed with water and aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The obtained residue was purified by column chromatography (hexane:ethyl acetate=1:2) to give the title compound (300 mg) as white amorphous.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate solution was washed with water and aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-ec23673e034e4751a74ae1b965a825a5
Source dataset
uspto-grants-2014_02
Patent number
US08658639B2

Reaction notes

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