Dimethylformamide dimethyl acetal → HCID 86652978, compound

HRID 1408557Notes

Reaction equation

HRID 1408557 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[C:14]([F:15])=[CH:13][C:12]([NH:16][C:17](=[O:22])[CH2:18][C:19](=[O:21])[CH3:20])=[CH:11][C:10]=3[F:23])[N:7]=[C:6]([C:24]([F:27])([F:26])[F:25])[CH:5]=2)[CH2:3][CH2:2]1.CO[CH:30](OC)[N:31]([CH3:33])[CH3:32]>>[CH:1]1([C:4]2[N:8]([C:9]3[C:10]([F:23])=[CH:11][C:12]([NH:16][C:17](=[O:22])[C:18](=[CH:30][N:31]([CH3:33])[CH3:32])[C:19](=[O:21])[CH3:20])=[CH:13][C:14]=3[F:15])[N:7]=[C:6]([C:24]([F:27])([F:26])[F:25])[CH:5]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 86702419HCID 86702419, compound

Product 1

HCID 86652978HCID 86652978, compoundYield 60.9%

Procedure

N-{4-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-3,5-difluorophenyl)-3-oxobutanamide (1 g, 2.6 mmol) and N,N-Dimethylformamide dimethylacetal (1.7 g, 14.2 mmol) were mixed and stirred at rt for overnight. Workup (AcOEt/H2O) followed by purification on 60-120 mesh silicagel using AcOEt and Peteher (1:1) as eluent afforded N-{4-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-3,5-difluorophenyl}-2-[(dimethylamino)methylene]-3-oxobutanamide (0.7 g).

Workup

  1. customWorkup (AcOEt/H2O) followed by purification on 60-120 mesh silicagel

Sources & evidence

ORD record
ord-d2b10a48583145b1a09f567fe432b3e8
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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