Acetic Acid → 3-(2-(Trifluoromethyl)pyridin-4-ylamino)cyclopent-2-enone

HRID 927202Notes

Reaction equation

HRID 927202 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][C:3](=[O:6])[CH2:2]1.[F:8][C:9]([F:18])([F:17])[C:10]1[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][N:11]=1.C(O)(=O)C>O.CO>[F:18][C:9]([F:8])([F:17])[C:10]1[CH:15]=[C:14]([NH:16][C:1]2[CH2:5][CH2:4][C:3](=[O:6])[CH:2]=2)[CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 774661,3-CyclopentanedioneHCID 102613882-(Trifluoromethyl)pyridin-4-amine

Product 1

HCID 903110023-(2-(Trifluoromethyl)pyridin-4-ylamino)cyclopent-2-enone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of cyclopentane-1,3-dione (1.51 g, 15.4 mmol), 2-(trifluoromethyl)pyridin-4-amine (2.50 g, 15.4 mmol) and acetic acid (7.5 mL) is heated at 130° C. for 5 h, cooled at room temperature, diluted with water and methanol, and purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% formic acid). Yield: 2.26 g; ESI mass spectrum [M+H]+=243; Retention time HPLC: 0.77 min (Z018_S04).

Workup

  1. temperaturecooled at room temperature
  2. custompurified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% formic acid)
  3. custom0.77 min (Z018_S04)

Sources & evidence

ORD record
ord-8eb5b5df1fd243fc9ca3e86f74c86a21
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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