Methyl 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate → Methyl 2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-5-(4-methylpentanoyl)-1,4-dihydro-pyridine-3-carboxylate

HRID 1669795Notes

Reaction equation

HRID 1669795 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](=[CH:25][C:26](=[O:32])[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH3:24]>C(O)C>[CH3:20][C:19]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:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 67342184Methyl 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoateHCID 714061112-Amino-7-methyloct-2-en-4-one

Product 1

HCID 57503352Methyl 2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-5-(4-methylpentanoyl)-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 35 mg (0.227 mmol) of 2-amino-7-methyloct-2-en-4-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 45.3 mg (61% 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-36e803bb62e94258a66bd47966deb09e
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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