Sodium hydride → HCID 178448674, compound

HRID 2243209Notes

Reaction equation

HRID 2243209 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[CH2:8][C:7](=[O:11])[N:6]1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[S:25](=[O:33])(=[O:32])[N:24]=1>C1COCC1>[C:1]([N:5]1[C:9]([OH:10])=[C:8]([C:23]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[S:25](=[O:32])(=[O:33])[N:24]=2)[C:7](=[O:11])[N:6]1[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 64783Pseudosaccharin chlorideHCID 57434339HCID 57434339, compound

Product 1

HCID 178448674HCID 178448674, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

step 5—To a solution of the pyrazolone 62a (300 mg, 1.1 mmol) in THF (5 mL) was added NaH (54 mg, 1.4 mmol). The reaction mixture was stirred at RT for 20 min, and 3-chloro-benzo[d]isothiazole 1,1-dioxide (270 mg, 1.4 mmol) was added. The reaction mixture was then stirred at RT for 2 h, quenched with saturated aqueous NH4Cl and extracted into ethyl acetate (2×). The combined organics were dried (MgSO4), filtered and the solvent was removed under reduced pressure. The crude product was purified by reverse-phase column chromatography eluting with acetonitrile/water which afforded 15 mg (3%) of III-2; LCMS RT 2.3 min, M−H.

Workup

  1. stirringThe reaction mixture was then stirred at RT for 2 h
  2. customquenched with saturated aqueous NH4Cl
  3. extractionextracted into ethyl acetate (2×)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was purified by reverse-phase column chromatography
  8. washeluting with acetonitrile/water which
  9. customafforded 15 mg (3%) of III-2

Sources & evidence

ORD record
ord-01a024eeb8674ccead018d37908f0e2f
Source dataset
uspto-grants-2010_03
Patent number
US07674810B2

Reaction notes

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