Dimethylformamide dimethyl acetal → HCID 66710833, compound

HRID 2089761Notes

Reaction equation

HRID 2089761 reaction equation
[C:1]([C:4]1[C:9](=[O:10])[C:8]([CH3:11])=[CH:7][N:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:5]=1)(=[O:3])[CH3:2].CO[CH:24](OC)[N:25]([CH3:27])[CH3:26]>>[CH3:24][N:25]([CH3:27])[CH:26]=[CH:2][C:1]([C:4]1[C:9](=[O:10])[C:8]([CH3:11])=[CH:7][N:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=2)[N:5]=1)=[O:3]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 59436279HCID 59436279, compound

Product 1

HCID 66710833HCID 66710833, compoundYield 87%

Conditions

Temperature
120 °C

Procedure

A microwave vial containing 3-acetyl-5-methyl-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.363 g, 1.2 mmol) and N,N-dimethylformamide dimethylacetal (2.5 mL) was heated at 120° C. for 20 min. The crude material was concentrated and purified by flash column chromatography (silica gel; methylene chloride to 1:9 methanol/methylene chloride) to provide 3-[3-(dimethylamino)prop-2-enoyl]-5-methyl-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.365 g, 87%) as an orange solid.

Workup

  1. concentrationThe crude material was concentrated
  2. custompurified by flash column chromatography (silica gel; methylene chloride to 1:9 methanol/methylene chloride)

Sources & evidence

ORD record
ord-46e95364731e42de8dab6e6dfd097fae
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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