Dimethylformamide dimethyl acetal → Methyl 1-(2,5-difluoro-4-morpholin-4-ylphenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylate

HRID 1407229Notes

Reaction equation

HRID 1407229 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:5]([F:14])=[CH:4][C:3]=1[NH:15][N:16]=[C:17]([C:22](=[O:26])[CH2:23][O:24][CH3:25])[C:18]([O:20][CH3:21])=[O:19].[CH3:27]OC(OC)N(C)C>>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:5]([F:14])=[CH:4][C:3]=1[N:15]1[CH:27]=[C:23]([O:24][CH3:25])[C:22](=[O:26])[C:17]([C:18]([O:20][CH3:21])=[O:19])=[N:16]1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178496285HCID 178496285, compound

Product 1

HCID 58072338Methyl 1-(2,5-difluoro-4-morpholin-4-ylphenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylateYield 95%

Procedure

A solution of methyl 2-[(2,5-difluoro-4-morpholin-4-ylphenyl)hydrazono]-4-methoxy-3-oxobutanoate (2.8 g, 7.5 mmol) in N,N-dimethylformamide dimethyl acetal (18 mL) was stirred at 100° C. for 80 min. After cooling to room temperature, the precipitate was collected by filtration and washed with iPr2O to give the title compound (2.7 g, 95% yield) as a brown powder: 1H NMR (300 MHz, DMSO-d6): δ ppm 3.12 (4H, dt, J=4.4, 2.5 Hz), 3.48-4.31 (10H, m), 7.18 (1H, dd, J=12.5, 7.6 Hz), 7.72 (1H, dd, J=12.5, 7.2 Hz), 8.50 (1H, s). LC-MS (ESI) m/z 382 [M+H]+.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with iPr2O

Sources & evidence

ORD record
ord-635253fedbc74f129bb62a6e4c161a87
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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