Acetic Acid → HCID 86732347, compound

HRID 517224Notes

Reaction equation

HRID 517224 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[NH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1.C(O)(=O)C>C(OCC)(=O)C>[F:19][C:16]([F:17])([F:18])[C:12]1[CH:11]=[C:10]([NH:9][C:1]2[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH:2]=2)[CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 104341,3-CyclohexanedioneHCID 102613882-(Trifluoromethyl)pyridin-4-amine

Product 1

HCID 86732347HCID 86732347, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of cyclohexane-1,3-dione (2.00 g, 17.8 mmol), 4-amino-2-trifluormethylpyridine (2.89 g, 17.8 mmol) and glacial acetic acid (10 mL) is heated at 130° C. for 4 h. The mixture cooled at room temperature, diluted with ethyl acetate and extracted three times with water. The phases are separated, and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried over Na2SO4 and concentreated under reduced pressure. The residue is purified by flash chromatography on silica (gradient dichloromethane/is methanol 95:5). Yield: 940 mg; ESI mass spectrum [M+H]+=257; Retention time HPLC: 0.80 min (V011_S01).

Workup

  1. temperatureThe mixture cooled at room temperature
  2. extractionextracted three times with water
  3. customThe phases are separated
  4. extractionthe aqueous layer is extracted with ethyl acetate
  5. dry with materialThe combined organic layers are dried over Na2SO4
  6. customThe residue is purified by flash chromatography on silica (gradient dichloromethane/is methanol 95:5)
  7. custom0.80 min (V011_S01)

Sources & evidence

ORD record
ord-8d35a4dd770c42f381abdc057c4c0675
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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