4-Amino-1-cyclobutylpent-3-en-2-one → Methyl 5-(cyclobutylacetyl)-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydro-pyridine-3-carboxylate

HRID 1669797Notes

Reaction equation

HRID 1669797 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:19](=O)[CH3:20])[C:15]([O:17][CH3:18])=[O:16].[NH2:22][C:23]([CH3:32])=[CH:24][C:25](=[O:31])[CH2:26][CH:27]1[CH2:30][CH2:29][CH2:28]1>C(O)C>[CH:27]1([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:14]([C:15]([O:17][CH3:18])=[O:16])=[C:19]([CH3:20])[NH:22][C:23]=2[CH3:32])=[O:31])[CH2:28][CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 669915394-Amino-1-cyclobutylpent-3-en-2-oneHCID 67342184Methyl 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate

Product 1

HCID 15979037Methyl 5-(cyclobutylacetyl)-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydro-pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

50 mg (0.175 mmol) of methyl 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate are dissolved with 34.7 mg (0.227 mmol) of 4-amino-1-cyclobutylpent-3-en-2-one in 3 ml of ethanol and heated under reflux under argon for 24 h. The reaction mixture is purified by preparative HPLC. Concentration of the fractions results in 36 mg (43% of theory) of the title compound as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 24 h
  3. customThe reaction mixture is purified by preparative HPLC

Sources & evidence

ORD record
ord-0f023f96c44e4c8c85c9dd3d55d4465b
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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