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

HRID 557408Notes

Reaction equation

HRID 557408 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](=[CH:25][C:26](=[O:32])[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH3:24].C(O)(=O)C>CC(O)C>[CH3:19][C:18]1[NH:22][C:23]([CH3:24])=[C:25]([C:26](=[O:32])[CH2:27][CH2:28][CH:29]([CH3:30])[CH3:31])[CH:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:17]=1[C:15]#[N:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 133748832-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 159792222,6-Dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-5-(4-methylpentanoyl)-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, 82.4 mg (0.53 mmol) of 2-amino-7-methyloct-2-en-4-one (example 14, stage a) and 31.9 mg (0.53 mmol) of acetic acid in 5 ml of 2-propanol and heated under reflux under argon for 6 h. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. 47 mg (22% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 6 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-f4c4944f4a5c47a1a621048d09bd5665
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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