Dimethylformamide dimethyl acetal → HCID 58072210, compound

HRID 1624701Notes

Reaction equation

HRID 1624701 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[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[C:7]([F:8])=[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[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 178496280HCID 178496280, compound

Product 1

HCID 58072210HCID 58072210, compoundYield 84%

Procedure

A solution of methyl 2-[(2,3-difluoro-4-morpholin-4-ylphenyl)hydrazono]-4-methoxy-3-oxobutanoate (4.7 g, 13 mmol) in N,N-dimethylformamide dimethyl acetal (20 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 (4.1 g, 84% yield) as a brown powder: NMR (300 MHz, DMSO-d6): δ ppm 3.13 (4H, dt, J=4.4, 2.5 Hz), 3.49-4.05 (10H, m), 7.03 (1H, td, J=8.8, 2.5 Hz), 7.51 (1H, td, J=8.5, 2.3 Hz), 8.53 (1H, d, J=1.5 Hz). 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-470b318fb364479a83c534bb27aecd1a
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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