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

HRID 557413Notes

Reaction equation

HRID 557413 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.[C:17]([CH:19]=[C:20]([O-])[CH3:21])#[N:18].[Na+].[NH2:24][C:25](=[CH:27][C:28](=[O:34])[CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[CH3:26].C(O)(=O)C>CC(O)C>[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([CH:13]2[C:27]([C:28](=[O:34])[CH2:29][CH2:30][CH:31]([CH3:32])[CH3:33])=[C:25]([CH3:26])[NH:24][C:20]([CH3:21])=[C:19]2[C:17]#[N:18])=[C:8]2[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]([CH3:15])[O:7]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 574388895,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 714061112-Amino-7-methyloct-2-en-4-oneHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

Product 1

HCID 669920674-(5,6-Difluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-5-(4-methylpentanoyl)-1,4-dihydropyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 100 mg (0.45 mmol) of 5,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde in 5 ml of 2-propanol is mixed with 46.9 mg (0.45 mmol) of sodium 1-cyanoprop-1-en-2-olate, 69.25 mg (0.45 mmol) of 2-amino-7-methyloct-2-en-4-one (example 14, stage a) 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). 88.1 mg (46.36% of theory) of the title compound are obtained as yellow 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-c91b1e7ec6654c1fb1be7605852be108
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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