Dimethylformamide dimethyl acetal → HCID 86652979, compound

HRID 388852Notes

Reaction equation

[CH:1]1([C:4]2[N:8]([C:9]3[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:21])[CH2:17][C:18](=[O:20])[CH3:19])=[CH:11][N:10]=3)[N:7]=[C:6]([C:22]([F:25])([F:24])[F:23])[CH:5]=2)[CH2:3][CH2:2]1.CO[CH:28](OC)[N:29]([CH3:31])[CH3:30]>>[CH:1]1([C:4]2[N:8]([C:9]3[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:21])[C:17](=[CH:28][N:29]([CH3:31])[CH3:30])[C:18](=[O:20])[CH3:19])=[CH:11][N:10]=3)[N:7]=[C:6]([C:22]([F:24])([F:25])[F:23])[CH:5]=2)[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal

HCID 86702420HCID 86702420, compound

Product 1

HCID 86652979HCID 86652979, compoundYield 56.5%

Procedure

Step-2: N-{2-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidin-5-yl}-3-oxobutanamide (445 mg, 1.3 mmol) and N,N-Dimethylformamide dimethylacetal (859 mg, 7.2 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-{2-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]pyrimidin-5-yl}-2-[(dimethylamino)methylene]-3-oxobutanamide (0.3 g).

Workup

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

Sources & evidence

ORD record: ord-e85f3bbaaedd435f85e04c43d25c26e1
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377970B2

Reaction notes

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