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

HRID 1669765Notes

Reaction equation

HRID 1669765 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](/[CH3:36])=[CH:28]\[C:29]([O:31][CH:32]1[CH2:35][CH2:34][CH2:33]1)=[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][CH:32]2[CH2:35][CH2:34][CH2:33]2)=[O:30])=[C:27]([CH3:36])[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 57475512Cyclobutyl 3-aminocrotonateHCID 673426642-[(2-Methyl-4-oxo-4H-chromen-8-yl)methylene]-1-phenylbutane-1,3-dione

Product 1

HCID 57503331Cyclobutyl 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

340 mg (1.02 mmol) of 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-1-phenylbutane-1,3-dione are dissolved with 156 mg (1.8 mmol) of cyclobutyl 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 206 mg (43% 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-5bfe87ba3bac4c1da4a2adfdb34b731d
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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