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

HRID 557411Notes

Reaction equation

HRID 557411 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]([CH3:35])=[CH:26][C:27](=[O:34])[CH2:28][CH2:29][CH:30]1[CH2:33][CH2:32][CH2:31]1.C(O)(=O)C>CC(O)C>[CH:30]1([CH2:29][CH2:28][C:27]([C:26]2[CH:13]([C:9]3[CH:10]=[C:11]([F:12])[C:2]([F:1])=[C:3]4[C:8]=3[O:7][C:6]([CH3:15])=[CH:5][C:4]4=[O:16])[C:19]([C:17]#[N:18])=[C:20]([CH3:21])[NH:24][C:25]=2[CH3:35])=[O:34])[CH2:31][CH2:32][CH2:33]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 574388895,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 669918105-Amino-1-cyclobutylhex-4-en-3-oneHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

Product 1

HCID 159792255-(3-Cyclobutylpropanoyl)-4-(5,6-difluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-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, 74.61 mg (0.45 mmol) of 5-amino-1-cyclobutylhex-4-en-3-one (example 15, 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). 71.2 mg (36.4% 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-b2097ab313704baba3b045eaba2b416a
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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