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

HRID 870451Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:19][C:20]([C:22]2[C:23](=[O:35])[N:24]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:25]([CH3:28])[C:26]=2[CH3:27])=[O:21])=[CH:4][C:5]([F:18])=[C:6]([CH:17]=1)[O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10](C(N)=O)[CH:9]=1.C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C.CC#[N:53]>CCOC(C)=O.O>[NH2:53][C:10]1[CH:9]=[C:8]([O:7][C:6]2[C:5]([F:18])=[CH:4][C:3]([NH:19][C:20]([C:22]3[C:23](=[O:35])[N:24]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:25]([CH3:28])[C:26]=3[CH3:27])=[O:21])=[C:2]([Cl:1])[CH:17]=2)[CH:13]=[CH:12][N:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 4-(5-chloro-4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)picolinamide (297.6 mg, 0.6 mmol) in EtOAc (4 mL), CH3CN (4 mL) and H2O (2 mL) was added PhI(OAc)2 (97 mg, 0.3 mmol) at 0° C., the mixture was stirred at 0° C. for 30 minutes, then warmed up to rt and stirred for 12 hours. The mixture was concentrated in vacuo and the residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=20/1) to give the title compound as a light beige solid (220 mg, 78.3%).

Workup

temperaturewarmed up to rt
stirringstirred for 12 hours
concentrationThe mixture was concentrated in vacuo
customthe residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=20/1)

Sources & evidence

ORD record: ord-b648cb88377c40d785447a08bbb85d98
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969388B1

Reaction notes

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