Water → HCID 21881989, compound

HRID 721977Notes

Reaction equation

HRID 721977 reaction equation
[CH3:1][C:2]([C:5]1[CH:9]=[CH:8][NH:7][N:6]=1)([CH3:4])[CH3:3].[H-].[Na+].CS(O)(=O)=O.O[CH:18]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[C:19]1=[O:33].O>CN(C)C=O>[CH3:1][C:2]([C:5]1[CH:9]=[CH:8][N:7]([CH:18]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:30])[F:31])[CH:24]=3)[C:19]2=[O:33])[N:6]=1)([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 86608403HCID 86608403, compoundHCID 178441177HCID 178441177, compound

Product 1

HCID 21881989HCID 21881989, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(1,1-dimethylethyl)1H-pyrazole (0.22 g, 1.8 mmol) in N,N-dimethylformamide (20 mL) under nitrogen at room temperature was added 60% sodium hydride in mineral oil (90 mg, 2.16 mmol). After the addition, the mixture was stirred at room temperature for ˜15 minutes, and 3-hydroxy-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone methanesulfonate (0.5 g, 1.8 mmol) was added. The resulting reaction mixture was stirred at room temperature overnight and then poured into water (˜100 mL). The aqueous layer was extracted twice with ethyl acetate (˜30 mL each; brine solution was added to separate the two layers). The organic extracts were combined, dried over MgSO4 and filtered. The filtrate was concentrated and the residue purified by column chromatography (silica gel, ˜20% ethyl acetate/80% hexanes) to give the title compound, a compound of this invention, as a yellow solid (300 mg) melting at 76–78° C.

Workup

  1. additionAfter the addition
  2. customThe resulting reaction mixture
  3. stirringwas stirred at room temperature overnight
  4. extractionThe aqueous layer was extracted twice with ethyl acetate (˜30 mL each
  5. additionbrine solution was added
  6. customto separate the two layers)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. customthe residue purified by column chromatography (silica gel, ˜20% ethyl acetate/80% hexanes)

Sources & evidence

ORD record
ord-100ad81cf25b4615870d439302ea660d
Source dataset
uspto-grants-2006_11
Patent number
US07138361B2

Reaction notes

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