Dimethylformamide dimethyl acetal → HCID 66710620, compound

HRID 1407144Notes

Reaction equation

HRID 1407144 reaction equation
[C:1]([C:4]1[C:9](=[O:10])[C:8]([O:11][CH3:12])=[CH:7][N:6]([C:13]2[C:21]3[O:20][C:19]([F:23])([F:22])[O:18][C:17]=3[CH:16]=[CH:15][CH:14]=2)[N:5]=1)(=[O:3])[CH3:2].CO[CH:26](OC)[N:27]([CH3:29])[CH3:28]>>[F:23][C:19]1([F:22])[O:18][C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([N:6]3[CH:7]=[C:8]([O:11][CH3:12])[C:9](=[O:10])[C:4]([C:1](=[O:3])[CH:2]=[CH:26][N:27]([CH3:29])[CH3:28])=[N:5]3)[C:21]=2[O:20]1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 59436162HCID 59436162, compound

Product 1

HCID 66710620HCID 66710620, compoundYield 74%

Procedure

A solution of 3-acetyl-1-(2,2-difluoro-1,3-benzodioxol-4-yl)-5-methoxypyridazin-4(1H)-one (2.3 g, 7.1 mmol) in N,N-dimethylformamide dimethyl acetal (75 mL) was refluxed for 3 h. The mixture was concentrated under reduced pressure. The brown crystals were washed with AcOEt/hexane (1/1) to give the title compound (2.0 g, 74% yield) as yellow crystals: 1H NMR (300 MHz, CDCl3): δ ppm 2.91 (3H, s), 3.14 (3H, s), 3.94 (3H, s), 5.78 (1H, d, J=11.7 Hz), 7.10 (1H, dd, J=8.3, 1.1 Hz), 7.23 (1H, t, J=8.3 Hz), 7.63 (1H, d, J=8.7 Hz), 7.79 (1H, brs), 8.03 (1H, s).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washThe brown crystals were washed with AcOEt/hexane (1/1)

Sources & evidence

ORD record
ord-807be7b8ef964cbf9916a2a5ba1b7def
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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