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

HRID 557441Notes

Reaction equation

HRID 557441 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=O.[C:15]([CH:17]=[C:18]([O-])[CH3:19])#[N:16].[Na+].[NH2:22][C:23]([CH3:33])=[CH:24][C:25](=[O:32])[CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.C(O)(=O)C>CC(O)C>[CH:27]1([CH2:26][C:25]([C:24]2[CH:13]([C:5]3[CH:6]=[CH:7][CH:8]=[C:9]4[C:4]=3[O:3][C:2]([CH3:1])=[CH:11][C:10]4=[O:12])[C:17]([C:15]#[N:16])=[C:18]([CH3:19])[NH:22][C:23]=2[CH3:33])=[O:32])[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 669917234-Amino-1-cyclopentylpent-3-en-2-oneHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

Product 1

HCID 669918735-(Cyclopentylacetyl)-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

150 mg (0.79 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 84 mg (0.79 mmol) of sodium 1-cyanoprop-1-en-2-olate, 133 mg (0.79 mmol) of 4-amino-1-cyclopentylpent-3-en-2-one and 68 μl (1.19 mmol) of acetic acid in 4 ml of 2-propanol and heated under reflux under argon for 4 h. After cooling, the suspension is filtered with suction and the remaining solid is washed with diethyl ether (20 ml). 240 mg (75% of theory) of the title compound are obtained as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 4 h
  3. temperatureAfter cooling
  4. filtrationthe suspension is filtered with suction
  5. washthe remaining solid is washed with diethyl ether (20 ml)

Sources & evidence

ORD record
ord-5b5b22c30a584b27a7d1be011192e9a6
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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