2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → Ethyl 5-benzoyl-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

HRID 1669764Notes

Reaction equation

HRID 1669764 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](/[CH3:34])=[CH:28]\[C:29]([O:31][CH2:32][CH3:33])=[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][CH2:32][CH3:33])=[O:30])=[C:27]([CH3:34])[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 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 673426642-[(2-Methyl-4-oxo-4H-chromen-8-yl)methylene]-1-phenylbutane-1,3-dione

Product 1

HCID 16045280Ethyl 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

353 mg (1.06 mmol) of 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-1-phenylbutane-1,3-dione are dissolved with 137 mg (1.06 mmol) of ethyl 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 245 mg (52% 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-6145027fff3d4c7fb532a2e45ba24f05
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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