Acetic Acid → 4-(5,6-Difluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-5-(3-methylbutanoyl)-1,4-dihydropyridine-3-carbonitrile

HRID 557412Notes

Reaction equation

HRID 557412 reaction equation
[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([CH:13]=O)=[C:8]2[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]([CH3:15])[O:7]2.CC(O)C.[C:21]([CH:23]=[C:24]([O-])[CH3:25])#[N:22].[Na+].[NH2:28][C:29](=[CH:31][C:32](=[O:37])[CH2:33][CH:34]([CH3:36])[CH3:35])[CH3:30].C(O)(=O)C>>[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([CH:13]2[C:31]([C:32](=[O:37])[CH2:33][CH:34]([CH3:36])[CH3:35])=[C:29]([CH3:30])[NH:28][C:24]([CH3:25])=[C:23]2[C:21]#[N:22])=[C:8]2[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]([CH3:15])[O:7]2

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 3776IsopropanolHCID 574388895,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 714061102-Amino-6-methylhept-2-en-4-oneHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

Product 1

HCID 159793464-(5,6-Difluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-5-(3-methylbutanoyl)-1,4-dihydropyridine-3-carbonitrile

Procedure

A solution of 100 mg (0.45 mmol) of 5,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde in ml of 2-propanol is mixed with 46.9 mg (0.45 mmol) of sodium 1-cyanoprop-1-en-2-olate, 63 mg (0.45 mmol) of 2-amino-6-methylhept-2-en-4-one and 0.04 ml (0.67 mmol) of acetic acid and stirred under reflux for 3 h. After cooling, the mixture is concentrated. The residue is purified on an Analogix cartridge (F12M) (mobile phase: cyclohexane/ethyl acetate 2:1). 20.9 mg (11.36% of theory) of the title compound are obtained as white crystals.

Workup

  1. temperatureunder reflux for 3 h
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. customThe residue is purified on an Analogix cartridge (F12M) (mobile phase: cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-55fbf5ad6cae4d26a9f5f419077f971b
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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