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

HRID 870432Notes

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]=[C:13]([F:15])[C:12]([NH:16][C:17]([C:19]2[C:20](=[O:32])[N:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:22]([CH3:25])[C:23]=2[CH3:24])=[O:18])=[CH:11][C:10]=1[F:33].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CC#[N:54]>CCOC(C)=O.O>[NH2:54][C:3]1[C:2]([Cl:1])=[C:7]([O:8][C:9]2[C:10]([F:33])=[CH:11][C:12]([NH:16][C:17]([C:19]3[C:20](=[O:32])[N:21]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:22]([CH3:25])[C:23]=3[CH3:24])=[O:18])=[C:13]([F:15])[CH:14]=2)[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)-2,5-difluorophenoxy)picolinamide (310 mg, 0.60 mmol) in EtOAc (6.0 mL), CH3CN (6.0 mL) and H2O (3.0 mL) at 0° C. was added iodobenzene diacetate (234 mg, 0.72 mmol). After stirring at 0° C. for 30 minutes, the mixture was allowed warm up to rt and stirred for 4 hours. The mixture was concentrated in vacuo and the residue was purified by a silica gel column chromatography (MeOH/DCM (v/v)=1/70) to give the title compound as a pale yellow solid (200 mg, 69%).

Workup

temperaturethe mixture was allowed warm up to rt
stirringstirred for 4 hours
concentrationThe mixture was concentrated in vacuo
customthe residue was purified by a silica gel column chromatography (MeOH/DCM (v/v)=1/70)

Sources & evidence

ORD record: ord-fa60da1d669547f9bf28931266161f4a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969388B1

Reaction notes

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