Acetic Anhydride → N-(4-((2-acetamidopyridin-4-yl)oxy)-2,3-difluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 870423Notes

Reaction equation

HRID 870423 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[C:19](=[O:31])[N:20]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:21]([CH3:24])[C:22]=3[CH3:23])=[O:17])=[C:11]([F:32])[C:10]=2[F:33])[CH:5]=[CH:4][N:3]=1.CCN(CC)CC.[C:41](OC(=O)C)(=[O:43])[CH3:42]>>[C:41]([NH:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[C:19](=[O:31])[N:20]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:21]([CH3:24])[C:22]=3[CH3:23])=[O:17])=[C:11]([F:32])[C:10]=2[F:33])[CH:5]=[CH:4][N:3]=1)(=[O:43])[CH3:42]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 73053610N-(4-((2-aminopyridin-4-yl)oxy)-2,3-difluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Product 1

HCID 73053652N-(4-((2-acetamidopyridin-4-yl)oxy)-2,3-difluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 68.9%

Conditions

Temperature
35 °C

Procedure

To a suspension of N-(4-((2-aminopyridin-4-yl)oxy)-2,3-difluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (135 mg, 0.3 mmol) in acetic anhydride (6 mL) was added Et3N (0.4 mL, 2.9 mmol). The reaction mixture was stirred at 35° C. for 4 hours, then filtered, and the filter cake washed with PE (5 mL), EtOAc (5 mL) and CH3OH (2 mL) respectively to give the title compound as a beige solid (102 mg, 68.9%).

Workup

  1. filtrationfiltered
  2. washthe filter cake washed with PE (5 mL), EtOAc (5 mL) and CH3OH (2 mL) respectively

Sources & evidence

ORD record
ord-18ead92a8cab4b9089e85eb40ca39b3d
Source dataset
uspto-grants-2015_03
Patent number
US08969388B1

Reaction notes

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