Acetic Acid → HCID 57503365, compound

HRID 1669817Notes

Reaction equation

HRID 1669817 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](=O)[CH2:17][C:18](=[O:20])[CH3:19].[NH2:22][C:23]([CH3:33])=[CH:24][C:25]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])=[O:26].C(O)(=O)C>C(O)(C)C>[C:18]([C:17]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:24]([C:25]([O:27][CH2:28][C:29]([F:30])([F:32])[F:31])=[O:26])=[C:23]([CH3:33])[NH:22][C:16]=1[CH3:15])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31261AcetylacetoneHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 714019912,2,2-Trifluoroethyl 3-aminobut-2-enoate

Product 1

HCID 57503365HCID 57503365, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

100 mg (0.53 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 93.1 mg (0.93 mmol) of 2,4-pentanedione, 97 mg (0.53 mmol) of 2,2,2-trifluoroethyl 3-aminobut-2-enoate and 32 μl (0.55 mmol) of acetic acid in 5 ml of isopropanol and heated under reflux under argon for 10 h. The solvent is then removed in vacuo, and the residue is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 95:5). 28 mg (12% of theory) of the title compound are obtained as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-f5dc4948799b4d819d1b5d857f3990fd
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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