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

HRID 870417Notes

Reaction equation

[Cl:1][C:2]1[C:3](C(N)=O)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[C:19](=[O:31])[N:20]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:21]([CH3:24])[C:22]=2[CH3:23])=[O:17])=[CH:11][C:10]=1[F:32].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CC#[N:53]>CCOC(C)=O.O>[NH2:53][C:3]1[C:2]([Cl:1])=[C:7]([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])=[CH:11][C:10]=2[F:32])[CH:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 3-chloro-4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)picolinamide (437 mg, 0.88 mmol) in EtOAc (5 mL), CH3CN (5 mL) and H2O (2.5 mL) was added iodobenzene diacetate (341 mg, 1.06 mmol) at 0° C. The reaction was stirred at 0° C. for 30 minutes, then warmed up to rt and continued to stir for 3 hours. The mixture was concentrated in vacuo, and the residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=1/3) to give the title compound as a yellow solid (290 mg, 70.6%).

Workup

temperaturewarmed up to rt
stirringto stir for 3 hours
concentrationThe mixture was concentrated in vacuo
customthe residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=1/3)

Sources & evidence

ORD record: ord-b4f19bf0d5224160bf04d69c5e7318f8
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969388B1

Reaction notes

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