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

HRID 870428Notes

Reaction equation

HRID 870428 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([NH:10][C:11]2[C:26]([F:27])=[CH:25][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18](C(N)=O)[CH:17]=3)=[C:13]([F:28])[CH:12]=2)=[O:9])[C:4](=[O:29])[N:3]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O.C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C.CC#[N:54]>CCOC(C)=O>[NH2:54][C:18]1[CH:17]=[C:16]([O:15][C:14]2[C:13]([F:28])=[CH:12][C:11]([NH:10][C:8]([C:5]3[C:4](=[O:29])[N:3]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:2]([CH3:1])[C:6]=3[CH3:7])=[O:9])=[C:26]([F:27])[CH:25]=2)[CH:21]=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 76724Iodobenzene diacetateHCID 730509204-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2,5-difluorophenoxy)picolinamide

Product 1

HCID 73053611N-(4-((2-aminopyridin-4-yl)oxy)-2,5-difluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2,5-difluorophenoxy)picolinamide (80 mg, 0.17 mmol) in EtOAc (2 mL), CH3CN (2 mL), and H2O (1 mL) was added PhI(OAc)2 (70 mg, 1.2 mmol). The reaction was stirred at 0° C. for 30 minutes, then warmed up to rt and continued to stir for 8 hours. The mixture was filtered through a CELITE® pad, which was washed with EtOAc (30 mL). The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=20/1) to afford the tile compound as a white solid (51 mg, 68%).

Workup

  1. temperaturewarmed up to rt
  2. stirringto stir for 8 hours
  3. filtrationThe mixture was filtered through a CELITE® pad, which
  4. washwas washed with EtOAc (30 mL)
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=20/1)

Sources & evidence

ORD record
ord-eb5cde8518ca48338241cf3260cc537d
Source dataset
uspto-grants-2015_03
Patent number
US08969388B1

Reaction notes

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