Trifluoroacetic acid → HCID 10287760, compound

HRID 1268888Notes

Reaction equation

HRID 1268888 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8]/[C:9](/[CH3:16])=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][CH:7]=1.[C:17]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)#[N:18].[CH3:27][C:28](=O)[CH2:29][C:30](=[O:32])[CH3:31].FC(F)(F)C(O)=O>C(OC(C)C)(C)C>[C:30]([C:29]1[CH:23]([C:22]2[CH:25]=[CH:26][C:19]([C:17]#[N:18])=[CH:20][CH:21]=2)[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([CH3:16])[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[C:28]=1[CH3:27])(=[O:32])[CH3:31]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 31261AcetylacetoneHCID 660424-CyanobenzaldehydeHCID 14691153HCID 14691153, compound

Product 1

HCID 10287760HCID 10287760, compound

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

100 mg (0.46 mmol) Ethyl(2E)-3-{[3-(methyl)phenyl]amino}-2-butenoate, 75 mg. (0.57 mmol) 4-cyanobenzaldehyde, 38 mg (0.38 mmol) 2,4-pentanedione, and 87 mg (0.76 mmol) trifluoroacetic acid are dissolved in 2 ml diisopropyl ether. The reaction mixture is stirred under reflux overnight. After cooling down to room temperature, the solvent is removed in vacuo and the residue is purified by preparative HPLC.

Workup

  1. temperatureunder reflux overnight
  2. customthe solvent is removed in vacuo
  3. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-5327918501c54b99a771c6d242206bd6
Source dataset
uspto-grants-2007_04
Patent number
US07199136B2

Reaction notes

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