Acetic Acid → Cyclobutyl 2,6-dimethyl-4-(2-methyl-4-oxo-4h-chromen-8-yl)-5-(trifluoroacetyl)-1,4-dihydro-pyridine-3-carboxylate

HRID 1669757Notes

Reaction equation

HRID 1669757 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]=O.[CH3:15][C:16]([CH2:18][C:19]([C:21]([F:24])([F:23])[F:22])=[O:20])=O.[NH2:25]/[C:26](/[CH3:35])=[CH:27]\[C:28]([O:30][CH:31]1[CH2:34][CH2:33][CH2:32]1)=[O:29].C(O)(=O)C>CC(O)C>[CH3:35][C:26]1[NH:25][C:16]([CH3:15])=[C:18]([C:19](=[O:20])[C:21]([F:24])([F:23])[F:22])[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:27]=1[C:28]([O:30][CH:31]1[CH2:32][CH2:33][CH2:34]1)=[O:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 57475512Cyclobutyl 3-aminocrotonate

Product 1

HCID 57503326Cyclobutyl 2,6-dimethyl-4-(2-methyl-4-oxo-4h-chromen-8-yl)-5-(trifluoroacetyl)-1,4-dihydro-pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

100 mg (0.53 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 143.3 mg (0.93 mmol) of 1,1,1-trifluoroacetylacetone, 82.4 mg (0.53 mmol) of cyclobutyl 3-aminocrotonate and 31.9 mg (0.53 mmol) of acetic acid in 5 ml of 2-propanol and heated to reflux under argon for 10 h. The solvent is removed in vacuo, and the residue is purified by column chromatography (mobile phase: dichloromethane/methanol 95:5). 8 mg (3.2% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureto reflux under argon for 10 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by column chromatography (mobile phase: dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-57959912e27c46de8c079cec2aef17af
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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