Hydrogen Peroxide → 2-(2,3-Dihydroxy-propylamino)-4-(6,6-dimethyl-4-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-indazol-1-yl)-benzamide

HRID 602412Notes

Reaction equation

HRID 602412 reaction equation
[OH:1][CH:2]([CH2:29][OH:30])[CH2:3][NH:4][C:5]1[CH:12]=[C:11]([N:13]2[C:21]3[CH2:20][C:19]([CH3:23])([CH3:22])[CH2:18][C:17](=[O:24])[C:16]=3[C:15]([C:25]([F:28])([F:27])[F:26])=[N:14]2)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8].[OH-:31].[Na+].OO>CCO.O>[OH:1][CH:2]([CH2:29][OH:30])[CH2:3][NH:4][C:5]1[CH:12]=[C:11]([N:13]2[C:21]3[CH2:20][C:19]([CH3:22])([CH3:23])[CH2:18][C:17](=[O:24])[C:16]=3[C:15]([C:25]([F:27])([F:28])[F:26])=[N:14]2)[CH:10]=[CH:9][C:6]=1[C:7]([NH2:8])=[O:31]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 669529362-(2,3-Dihydroxy-propylamino)-4-(6,6-dimethyl-4-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile

Product 1

HCID 118546912-(2,3-Dihydroxy-propylamino)-4-(6,6-dimethyl-4-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-indazol-1-yl)-benzamideYield 29.5%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

2-(2,3-Dihydroxy-propylamino)-4-(6,6-dimethyl-4-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile (1.7 g, 4 mmol, 1 eq), NaOH (806 mg, 20 mmol, 5 eq), and H2O2 (3 mL) were dissolved in EtOH-water (4:1) (40 mL). The mixture was microwaved at 120° C. for 15 min, then concentrated to dryness, and purified by flash chromatography, eluted by 10% MeOH in EtOAc to give pure 2-(2,3-Dihydroxy-propylamino)-4-(6,6-dimethyl-4-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-indazol-1-yl)-benzamide (0.52 g, 29% yield). LCMS (m/z): M+H=441.

Workup

  1. customThe mixture was microwaved at 120° C. for 15 min
  2. concentrationconcentrated to dryness
  3. custompurified by flash chromatography
  4. washeluted by 10% MeOH in EtOAc

Sources & evidence

ORD record
ord-a9620b1226514307b0ba7f9048b556c7
Source dataset
uspto-grants-2011_03
Patent number
US07906529B2

Reaction notes

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