Water → 5-fluoro-N-{2-[1-(isopropylamino)ethyl]phenyl}-1,3-dimethyl-1H-pyrazole-4-carboxamide

HRID 1176010Notes

Reaction equation

[F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9](Cl)=[O:10].[CH:12]([NH:15][CH:16]([C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20])[CH3:17])([CH3:14])[CH3:13].C(N(CC)CC)C.O>ClCCl>[F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9]([NH:20][C:19]1[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=1[CH:16]([NH:15][CH:12]([CH3:14])[CH3:13])[CH3:17])=[O:10]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 0.27 g (1.5 mmol) 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride in 10 ml dichloromethane is added dropwise to a solution of 0.27 g (1.5 mmol) 2-[1-(isopropylamino)ethyl]aniline (III-4) and 0.42 ml (3.0 mmol) triethylamine in 5 ml dichloromethane. The reaction mixture is stirred for 2 hours at 50° C. and thereafter for 16 hours at room temperature. The reaction mixture is worked up by adding it to water, then the organic phase is dried over magnesium sulfate and concentrated under vacuum. Column chromatography (4:1 hexane/acetone) yielded 0.27 g (56% of the theoretical yield) 5-fluoro-N-{2-[1-(isopropylamino)ethyl]phenyl}-1,3-dimethyl-1H-pyrazole-4-carboxamide [log P (pH 2.3)=0.58].

Workup

waitfor 16 hours at room temperature
dry with materialthe organic phase is dried over magnesium sulfate
concentrationconcentrated under vacuum
customColumn chromatography (4:1 hexane/acetone) yielded 0.27 g (56% of the

Sources & evidence

ORD record: ord-c65119153a33456d8d2f259009a70ce8
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842710B2

Reaction notes

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