Methyl 3-aminocrotonate → Methyl 5-benzoyl-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

HRID 1669767Notes

Reaction equation

HRID 1669767 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]=[C:14]([C:23](=O)[CH3:24])[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16].[NH2:26]/[C:27](/[CH3:33])=[CH:28]\[C:29]([O:31][CH3:32])=[O:30]>C(O)C>[C:15]([C:14]1[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:28]([C:29]([O:31][CH3:32])=[O:30])=[C:27]([CH3:33])[NH:26][C:23]=1[CH3:24])(=[O:16])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 643918Methyl 3-aminocrotonateHCID 673426642-[(2-Methyl-4-oxo-4H-chromen-8-yl)methylene]-1-phenylbutane-1,3-dione

Product 1

HCID 57503333Methyl 5-benzoyl-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

250 mg (0.75 mmol) of 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-1-phenylbutane-1,3-dione are dissolved with 116 mg (1.0 mmol) of methyl 3-aminocrotonate in 5 ml of ethanol and heated under reflux under argon for 24 h. The reaction solution is purified by preparative HPLC. Concentration of the product fractions and crystallization from ethyl acetate result in 158 mg (49% of theory) of the title compound as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 24 h
  3. customThe reaction solution is purified by preparative HPLC
  4. customConcentration of the product fractions and crystallization from ethyl acetate

Sources & evidence

ORD record
ord-b382571d4af346598d07e144758ca185
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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