Trifluoroacetic acid → HCID 86673604, compound

HRID 1023416Notes

Reaction equation

HRID 1023416 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.FC(F)(F)C(O)=O.[Cl:25][C:26]1[CH:31]=[C:30]([C:32](=O)[CH2:33][C:34](=O)[C:35]([F:38])([F:37])[F:36])[CH:29]=[CH:28][N:27]=1.[OH-].[Na+]>C(O)(C)C.O>[Cl:25][C:26]1[CH:31]=[C:30]([C:32]2[N:9]([C:6]3[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=3)[N:10]=[C:34]([C:35]([F:36])([F:37])[F:38])[CH:33]=2)[CH:29]=[CH:28][N:27]=1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 86673605HCID 86673605, compound

Product 1

HCID 86673604HCID 86673604, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

(4-Fluoro-phenyl)-hydrazine hydrochloride (95 mg, 0.57 mmol) is dissolved in isopropanol (3.0 mL) and triethylamine (0.08 mL, 0.57 mmol) is added. After the mixture is stirred for 5 min, trifluoroacetic acid (0.09 mL, 1.19 mmol) is added and the mixture is again stirred for 5 min Then 1-(2-Chloro-pyridin-4-yl)-4,4,4-trifluoro-butane-1,3-dione (130 mg, 0.52 mmol) is added and the reaction mixture is heated at 85° C. for 40 hrs and stirred at room temperature for another 48 hrs. Water (20 mL) is added and 1.0 M NaOH solution is used to adjust the pH to about 6. The reaction mixture is then extracted with EtOAc (3×20 ml) and the organic layers are combined and concentrated to give the crude product, which is used without purification.

Workup

  1. stirringthe mixture is again stirred for 5 min
  2. stirringstirred at room temperature for another 48 hrs
  3. extractionThe reaction mixture is then extracted with EtOAc (3×20 ml)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a858884afd0b44749735fa709bd99a01
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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