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

HRID 870422Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([NH:10][C:11]2[CH:26]=[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:27])[C:12]=2[F:28])=[O:9])[C:4](=[O:29])[N:3]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CC#[N:53]>CCOC(C)=O.O>[NH2:53][C:18]1[CH:17]=[C:16]([O:15][C:14]2[CH:25]=[CH:26][C:11]([NH:10][C:8]([C:5]3[C:4](=[O:29])[N:3]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:2]([CH3:1])[C:6]=3[CH3:7])=[O:9])=[C:12]([F:28])[C:13]=2[F:27])[CH:21]=[CH:20][N:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2,3-difluorophenoxy)picolinamide (108 mg, 0.22 mmol) in EtOAc (2.5 mL), CH3CN (2.5 mL) and H2O (1.5 mL) was added iodobenzene diacetate (96 mg, 0.30 mmol) at 0° C. The reaction was stirred at 0° C. for 30 minutes, then warmed up to rt and continued to stir for 4 hours. The mixture was concentrated in vacuo, and the residue was purified by a silica gel column chromatography (EtOAc/CH3OH (v/v)=10/1) to give the title compound as a pale yellow solid (32 mg, 32.3%).

Workup

temperaturewarmed up to rt
stirringto stir for 4 hours
concentrationThe mixture was concentrated in vacuo
customthe residue was purified by a silica gel column chromatography (EtOAc/CH3OH (v/v)=10/1)

Sources & evidence

ORD record: ord-e2afc043e6b44ac08e09bf439cf81287
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969388B1

Reaction notes

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