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

HRID 870434Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[NH:18][C:19]([C:21]1[C:22](=[O:34])[N:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:24]([CH3:27])[C:25]=1[CH3:26])=[O:20])[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8](C(N)=O)[CH:7]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CC#[N:52]>CCOC(C)=O.O>[NH2:52][C:8]1[CH:7]=[C:6]([O:5][C:4]2[CH:15]=[CH:16][C:17]([NH:18][C:19]([C:21]3[C:22](=[O:34])[N:23]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:24]([CH3:27])[C:25]=3[CH3:26])=[O:20])=[C:2]([Cl:1])[CH:3]=2)[CH:11]=[CH:10][N:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 4-(3-chloro-4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)phenoxy)picolinamide (160 mg, 0.33 mmol) in EtOAc (3 mL), CH3CN (2.5 mL) and H2O (1.3 mL) was added iodobenzene diacetate (130 mg, 0.40 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 (DCM/MeOH (v/v)=25/1) to give the title compound as a beige solid (100 mg, 67%).

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 (DCM/MeOH (v/v)=25/1)

Sources & evidence

ORD record: ord-b60f84bf747543ae9d66f309974ea185
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969388B1

Reaction notes

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