Water → HCID 10201733, compound

HRID 1168675Notes

Reaction equation

HRID 1168675 reaction equation
Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[N:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[C:3]=1[C:21]#[N:22].[NH:23]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[F-].[K+].O>CS(C)=O>[N:23]1([C:2]2[N:6]([C:7]3[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=3)[N:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[C:3]=2[C:21]#[N:22])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 8119AzepaneHCID 522689Potassium FluorideHCID 12087674HCID 12087674, compound

Product 1

HCID 10201733HCID 10201733, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
20 °C

Procedure

5—Chloro-(4-methanesulfonyl-phenyl)-3-trifluoromethyl-1H-pyrazole-4-carbonitrile (70 mg, 0.2 mmol) and azepane (40 mg, 0.4 mmol) were dissolved in dry dimethylsulfoxide (DMSO) (2 ml) and potassium fluoride (0.35 mg, 0.6 mmol) was added to the DMSO solution. The resulting mixture was stirred at 20° C. for a period of 48 hours. Analytical HPLC indicated the reaction completion. The reaction mixture was poured into water (15 ml) and the resulting mixture was extracted with ethyl acetate (20 ml). The organic extract was dried over magnesium sulfate and concentrated with a rotary evaporator. The desired product was isolated by chromatography on silica gel column. MS:395, r.t.: 2.6 min.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (20 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated with a rotary evaporator

Sources & evidence

ORD record
ord-1452fe3f66db406b82841edf171ad990
Source dataset
uspto-grants-2003_09
Patent number
US06627626B2

Reaction notes

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