Trifluoroacetic acid → HCID 58119790, compound

HRID 2368634Notes

Reaction equation

HRID 2368634 reaction equation
[NH2:1][C:2]([CH:16]([O:18][CH3:19])[CH3:17])=[CH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)=[O:5].FC(F)(F)C(O)=O.[CH3:27][C:28]1([CH3:36])[CH2:33][C:32](=O)[CH2:31][C:30](=[O:35])[CH2:29]1.[CH:37]1([CH:42]=O)[CH2:41][CH2:40][CH2:39][CH2:38]1>C(OC(C)C)(C)C>[CH:37]1([CH:42]2[C:31]3[C:30](=[O:35])[CH2:29][C:28]([CH3:27])([CH3:36])[CH2:33][C:32]=3[NH:1][C:2]([CH:16]([O:18][CH3:19])[CH3:17])=[C:3]2[C:4](=[O:5])[C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:14])([F:15])[F:13])=[CH:8][CH:7]=2)[CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 31358DimedoneHCID 70106CyclopentanecarbaldehydeHCID 66862226HCID 66862226, compound

Product 1

HCID 58119790HCID 58119790, compound

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

8.0 g 3-Amino-4-methoxy-1-(4-trifluoromethyl-phenyl)-pent-2-en-1-one are dissolved in 150 ml of diisopropylether, 2.2 ml trifluoroacetic acid and 4.1 g 5,5-dimethyl-cyclohexane-1,3-dione are successively added and the mixture is stirred for 10 minutes at room temperature. Then 3.75 ml cyclopentanecarbaldehyde are added and the mixture is heated for 15 hours to reflux at a dean-stark trap. After cooling to room temperature the solvents are evaporated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethylacetate 95:5 to 60:40). The product thus obtained is triturated with diisopropylether.

Workup

  1. temperaturethe mixture is heated for 15 hours
  2. temperatureto reflux at a dean-stark trap
  3. temperatureAfter cooling to room temperature the solvents
  4. customare evaporated in vacuo
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethylacetate 95:5 to 60:40)
  6. customThe product thus obtained
  7. customis triturated with diisopropylether

Sources & evidence

ORD record
ord-71f053784dcb425381e16103a6c03549
Source dataset
uspto-grants-2014_04
Patent number
US08703793B2

Reaction notes

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