Acetic Acid → HCID 57503335, compound

HRID 1669770Notes

Reaction equation

HRID 1669770 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.[NH2:15]/[C:16](/[CH3:23])=[CH:17]\[C:18]([O:20][CH2:21][CH3:22])=[O:19].[F:24][C:25]([F:33])([F:32])[C:26](=O)[CH2:27][C:28](=[O:30])[CH3:29].C(O)(=O)C>CC(O)C>[C:28]([C:27]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:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([CH3:23])[NH:15][C:26]=1[C:25]([F:33])([F:32])[F:24])(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 57503335HCID 57503335, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2.1 g (11.16 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde in 60 ml of 2-propanol is mixed with 1.44 g (11.16 mmol) of ethyl 3-aminocrotonate, 17.2 g (111.6 mmol) of 1,1,1-trifluoro-2,4-pentanedione and 0.96 ml (16.74 mmol) of acetic acid and stirred under reflux for 12 h. After cooling, the reaction mixture is concentrated and the residue is taken up in 30 ml of acetic acid and again stirred under reflux for 12 h. After cooling, the reaction mixture is concentrated, and the residue is purified by preparative HPLC. The product fractions are concentrated and purified again on an Analogix cartridge (mobile phase: cyclohexane/ethyl acetate 2:1). 0.212 g (4.4% of theory) of the title compound are obtained.

Workup

  1. temperatureunder reflux for 12 h
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated
  4. stirringagain stirred
  5. temperatureunder reflux for 12 h
  6. temperatureAfter cooling
  7. concentrationthe reaction mixture is concentrated
  8. customthe residue is purified by preparative HPLC
  9. concentrationThe product fractions are concentrated
  10. custompurified again on an Analogix cartridge (mobile phase: cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-87b09840d6794ccf912b76825f9a96a8
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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