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

HRID 557437Notes

Reaction equation

HRID 557437 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][CH2:27][CH:28]1[CH2:31][CH2:30][CH2:29]1.C(O)(=O)C>CC(O)C>[CH:28]1([CH2:27][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])[CH2:29][CH2:30][CH2:31]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 133748832-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 669917555-(3-Cyclobutylpropanoyl)-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

100 mg (0.53 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 55.8 mg (0.53 mmol) of sodium 1-cyanoprop-1-en-2-olate, 88.8 mg (0.53 mmol) of 5-amino-1-cyclobutylhex-4-en-3-one (example 15, stage a) and 30 μl (0.53 mmol) of acetic acid in 3 ml of 2-propanol and heated under reflux under argon for 4 h. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. 61 mg (28% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 4 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-aba788f6b0ad42b4b04f753a3f0132d8
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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