Water → HCID 73053628, compound

HRID 870441Notes

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:10]=[N:11][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:13][CH:14]=1.O.C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C.CC#[N:53]>CCOC(C)=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])=[N:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-chloro-4-((6-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)pyridin-3-yl)oxy)picolinamide (290 mg, 0.6 mmol) in EtOAc (4 mL), CH3CN (4 mL), and H2O (2 mL) was added PhI(OAc)2 (234 mg, 0.72 mmol). The reaction was stirred at 0° C. for 30 minutes, then warmed up to rt and continued to stir for 12 hours. The mixture was filtered through a CELITE® pad, which was washed with DCM (30 mL). The filtrate was washed with water (20 mL), then concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=50/1) to give the title compound as a light beige solid (120 mg, 44.7%).

Workup

temperaturewarmed up to rt
stirringto stir for 12 hours
filtrationThe mixture was filtered through a CELITE® pad, which
washwas washed with DCM (30 mL)
washThe filtrate was washed with water (20 mL)
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=50/1)

Sources & evidence

ORD record: ord-b7a181e3ae3a4aed96fa06b9cb4547c2
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969388B1

Reaction notes

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