Dimethylformamide dimethyl acetal → HCID 123973523, compound

HRID 1408555Notes

Reaction equation

HRID 1408555 reaction equation
[Cl:1][C:2]1[C:3]([C:23]([F:26])([F:25])[F:24])=[N:4][N:5]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:22])[CH2:18][C:19](=[O:21])[CH3:20])=[CH:12][CH:11]=2)[C:6]=1[CH:7]1[CH2:9][CH2:8]1.CO[CH:29](OC)[N:30]([CH3:32])[CH3:31]>>[Cl:1][C:2]1[C:3]([C:23]([F:24])([F:26])[F:25])=[N:4][N:5]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:22])[C:18](=[CH:29][N:30]([CH3:32])[CH3:31])[C:19](=[O:21])[CH3:20])=[CH:14][CH:15]=2)[C:6]=1[CH:7]1[CH2:8][CH2:9]1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 86702418HCID 86702418, compound

Product 1

HCID 123973523HCID 123973523, compoundYield 74.1%

Procedure

N-{4-[4-chloro-5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}-3-oxobutanamide (1.6 g, 3.98 mmol) and N,N-Dimethylformamide dimethylacetal (2.6 g, 21.9 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-[4-chloro-5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}-2-[(dimethylamino)methylene]-3-oxobutanamide (1.3 g).

Workup

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

Sources & evidence

ORD record
ord-b1eb9f096e3949a080039feccca7eca1
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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