Ethanol → 3-({4-[(dimethylamino)carbonyl]phenyl}amino)-1-phenyl-1H-pyrazole-4-carboxamide

HRID 1961509Notes

Reaction equation

[C:1]([C:3]1[C:4]([NH:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([N:21]([CH3:23])[CH3:22])=[O:20])=[CH:17][CH:16]=2)=[N:5][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1)#[N:2].[OH-].[Na+].CC[OH:30].OO>CS(C)=O.O>[CH3:22][N:21]([CH3:23])[C:19]([C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:4]2[C:3]([C:1]([NH2:2])=[O:30])=[CH:7][N:6]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:5]=2)=[CH:25][CH:24]=1)=[O:20]

Participants

Conditions

Temperature: 60 °C

Procedure

4-[(4-cyano-1-phenyl-1H-pyrazol-3-yl)amino]-N,N-dimethylbenzamide (83 mg, 0.250 mmol) and 5 N sodium hydroxide (0.351 mL, 1.753 mmol) were taken up in DMSO (1 mL)/EtOH (1 mL) and warmed to 60° C. Hydrogen peroxide (0.329 mL, 3.76 mmol) was added dropwise and stirring continued at 60° C. for 15 minutes. Room temperature was attained, water was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine (×2), dried over MgSO4 and concentrated in vacuo. Purification of the residue by MPLC (25-100% EtOAc-hexanes followed by 0-10% MeOH-EtOAc followed by 15% MeOH—CHCl3) gave 3-({4-[(dimethylamino)carbonyl]phenyl}amino)-1-phenyl-1H-pyrazole-4-carboxamide as a pale yellow solid.

Workup

customRoom temperature
extractionthe products extracted into EtOAc (×2)
washThe combined organic extracts were washed with brine (×2)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customPurification of the residue by MPLC (25-100% EtOAc-hexanes followed by 0-10% MeOH-EtOAc followed by 15% MeOH—CHCl3)

Sources & evidence

ORD record: ord-f4772a41617b4671b43021c07ec7b60b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415346B2

Reaction notes

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