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

HRID 1669784Notes

Reaction equation

HRID 1669784 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=[O:27])[C:10](=[CH:14][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[O:23][C:22]([CH3:25])=[CH:21][C:20]3=[O:26])[C:11](=O)[CH3:12])[CH:6]=[CH:7][CH:8]=1.[NH2:28]/[C:29](/[CH3:36])=[CH:30]\[C:31]([O:33][CH2:34][CH3:35])=[O:32]>CC(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[C:9]([C:10]1[CH:14]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[O:23][C:22]([CH3:25])=[CH:21][C:20]3=[O:26])[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:29]([CH3:36])[NH:28][C:11]=1[CH3:12])=[O:27]

Participants

4

Reactant 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 673429891-(3-Methoxyphenyl)-2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]butane-1,3-dione

Product 1

HCID 57503343Ethyl 5-(3-methoxybenzoyl)-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydro-pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

245 mg (0.67 mmol) of 1-(3-methoxyphenyl)-2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-butane-1,3-dione are heated with 87 mg (0.67 mmol) of ethyl 3-aminocrotonate in 5 ml of 2-propanol under reflux overnight. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. 102 mg (32% of theory) of the title compound are obtained.

Workup

  1. temperatureunder reflux overnight
  2. customThe solvent is removed in vacuo
  3. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-258847ba75c84da1aea856979bd39ff0
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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