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

HRID 557404Notes

Reaction equation

HRID 557404 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=O)=[C:8]2[C:3]=1[C:4](=[O:15])[CH:5]=[C:6]([CH3:14])[O:7]2.[C:16]([CH:18]=[C:19]([O-])[CH3:20])#[N:17].[Na+].[NH2:23][C:24]([CH3:33])=[CH:25][C:26](=[O:32])[CH2:27][CH:28]1[CH2:31][CH2:30][CH2:29]1.C(O)(=O)C>CC(O)C>[CH:28]1([CH2:27][C:26]([C:25]2[CH:12]([C:9]3[CH:10]=[CH:11][C:2]([F:1])=[C:3]4[C:8]=3[O:7][C:6]([CH3:14])=[CH:5][C:4]4=[O:15])[C:18]([C:16]#[N:17])=[C:19]([CH3:20])[NH:23][C:24]=2[CH3:33])=[O:32])[CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 574388885-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 669915394-Amino-1-cyclobutylpent-3-en-2-oneHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

Product 1

HCID 669921785-(Cyclobutylacetyl)-4-(5-fluoro-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 (0.49 mmol) of 5-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde in 5 ml of 2-propanol is mixed with 50.96 mg (0.49 mmol) of sodium 1-cyanoprop-1-en-2-olate, 92.90 mg (0.49 mmol) of 4-amino-1-cyclobutylpent-3-en-2-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 resulting residue is purified on an Analogix cartridge (F12M) (mobile phase: cyclohexane/ethyl acetate 2:1). 40.4 mg (20.5% 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 resulting residue is purified on an Analogix cartridge (F12M) (mobile phase: cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-0618a388c7b6455cb865205ebedefa4c
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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