Water → HCID 22316701, compound

HRID 497254Notes

Reaction equation

HRID 497254 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][CH:28]=4)=[CH:20][CH:19]=3)=[CH:16][C:15]([C:29]([F:32])([F:31])[F:30])=[N:14]2)[CH:6]=[CH:7][C:8]=1[S:9]([CH3:12])(=[O:11])=[O:10].[C:33]1(=[O:43])[NH:37][C:36](=[O:38])[C:35]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:34]12.[K].O>CN(C=O)C>[O:25]1[CH:26]=[CH:27][CH:28]=[C:24]1[C:21]1[CH:20]=[CH:19][C:18]([C:17]2[N:13]([C:5]3[CH:6]=[CH:7][C:8]([S:9]([CH3:12])(=[O:10])=[O:11])=[C:3]([CH:4]=3)[CH2:2][N:37]3[C:33](=[O:43])[C:34]4[C:35](=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:36]3=[O:38])[N:14]=[C:15]([C:29]([F:31])([F:32])[F:30])[CH:16]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 22316912HCID 22316912, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 22316701HCID 22316701, compoundYield 751.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-[3-chloromethyl-4-(methylsulfonyl)phenyl]-5-[4-(2-furyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole from step 1 of Example 160 (280 mg, 0.58 mmol) and potassium phthalimide (10 mg, 0.054 mmol) in DMF was heated at 90° C. for 1 hour. After cooled to room temperature, the mixture was poured into water (30 mL), and extracted with ether (30 mL×2), washed with water (30 mL) and brine (30 mL), dried over MgSO4, and concentrated in vacuo to give the title compound (240 mg, 70%).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionextracted with ether (30 mL×2)
  3. washwashed with water (30 mL) and brine (30 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb95bb318bf7491e9357da0f910a912b
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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