Dimethylformamide dimethyl acetal → HCID 59436171, compound

HRID 1895087Notes

Reaction equation

HRID 1895087 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:4]=[C:3]1[C:18]([NH2:20])=[O:19].CO[CH:23](OC)[N:24]([CH3:26])[CH3:25]>>[CH3:23][N:24]([CH:26]=[N:20][C:18]([C:3]1[C:2](=[O:1])[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:4]=1)=[O:19])[CH3:25]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 59436157HCID 59436157, compound

Product 1

HCID 59436171HCID 59436171, compoundYield 76%

Conditions

Temperature
130 °C

Procedure

A slurry of 4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxamide (0.54 g, 1.91 mmol) in N,N-dimethylformamide dimethylacetal (10 mL) was heated under microwave heating conditions at 130° C. for 15 min. After that time the reaction was cooled on an ice water bath and the resulting crystals collected by filtration and washed with hexanes to give 0.491 g (76%) of N-[(dimethylamino)methylidene]-4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxamide as off white crystals. 1H NMR (300 MHz, CDCl3) δ ppm 3.16 (s, 3H), 3.22 (s, 3H), 6.72 (d, J=8.1 Hz, 1H), 7.57-7.71 (m, 2H), 7.74-7.85 (m, 1H), 7.89 (s, 1H), 8.25 (d, J=8.1 Hz, 1H), 8.70 (s, 1H).

Workup

  1. temperatureAfter that time the reaction was cooled on an ice water bath
  2. filtrationthe resulting crystals collected by filtration
  3. washwashed with hexanes

Sources & evidence

ORD record
ord-b3e805094ab84fa98677ab24e869f7cc
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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