4-(Trifluoromethyl)benzoyl chloride → HCID 178523934, compound

HRID 2280408Notes

Reaction equation

HRID 2280408 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[S-:14][C:15]#[N:16].[K+].[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:36]=[C:35]([NH2:37])[NH:34][N:33]=2)=[C:28]([F:38])[CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:36]=[C:35]([NH:37][C:15]([NH:16][C:7](=[O:8])[C:6]3[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=3)=[S:14])[NH:34][N:33]=2)=[C:28]([F:38])[CH:27]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 516872Potassium thiocyanateHCID 178507294HCID 178507294, compound

Product 1

HCID 178523934HCID 178523934, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Trifluoromethylbenzoyl chloride (590 mg, 2.83 mmol) was dissolved in acetonitrile (˜30 mL) and potassium thiocyanate (302 mg, 3.22 mmol) was added to provide a reaction mixture. The reaction mixture was stirred at room temperature for 30 minutes, and then 3-(4-benzyloxy-2-fluoro-phenyl)-1H-pyrazol-5-amine (801 mg, 2.83 mmol) was added to the reaction mixture. Next, the reaction mixture was stirred at room temperature overnight, then concentrated in vacuo, slurried with water, and collected by filtration. The wet solid was held under heated vacuum for 24 hours to provide the title compound in 81% yield.

Workup

  1. customto provide a reaction mixture
  2. stirringNext, the reaction mixture was stirred at room temperature overnight
  3. concentrationconcentrated in vacuo
  4. filtrationcollected by filtration
  5. temperatureunder heated vacuum for 24 hours

Sources & evidence

ORD record
ord-bd7ca3d8e488436982ea68bb3f4775c1
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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