Dimethylsulfoxide ethanol → 4-(3-Cyclopropylmethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzamide

HRID 602409Notes

Reaction equation

HRID 602409 reaction equation
[CH:1]1([CH2:4][C:5]2[C:13]3[C:12](=[O:14])[CH2:11][C:10]([CH3:16])([CH3:15])[CH2:9][C:8]=3[N:7]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[N:6]=2)[CH2:3][CH2:2]1.CC[OH:27].CS(C)=O>[OH-].[Na+].OO.[Cl-].[Na+].O>[CH:1]1([CH2:4][C:5]2[C:13]3[C:12](=[O:14])[CH2:11][C:10]([CH3:16])([CH3:15])[CH2:9][C:8]=3[N:7]([C:17]3[CH:18]=[CH:19][C:20]([C:21]([NH2:22])=[O:27])=[CH:23][CH:24]=3)[N:6]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 22338741Dimethylsulfoxide ethanolHCID 669524354-(3-Cyclopropylmethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile

Product 1

HCID 118546884-(3-Cyclopropylmethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzamideYield 43%

Reagents, catalysts & solvents 3

HCID 784Hydrogen PeroxideSolventHCID 14798Sodium HydroxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

After dissolving the nitrile in 10 mL of 4:1 EtOH-DMSO, approximately 0.1 mL of 1 N NaOH (aq.) and 0.1 mL of 30% H2O2 (aq.) were added and the solution stirred for 1.5 hours. The reaction mixture was poured into brine, extracted with EtOAc (×3), and the combined organics washed with brine (×2). The organic extracts were dried over Na2SO4 and concentrated in vacuo to afford 73.2 mg (43% yield) of 4-(3-Cyclopropylmethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzamide as an off-white solid. LCMS (m/z): M+H=339.4.

Workup

  1. additionwere added
  2. extractionextracted with EtOAc (×3)
  3. washthe combined organics washed with brine (×2)
  4. dry with materialThe organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f212a023d0e4e9a90e893deb5af5a70
Source dataset
uspto-grants-2011_03
Patent number
US07906529B2

Reaction notes

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