Hydrogen Peroxide → HCID 59251071, compound

HRID 218153Notes

Reaction equation

HRID 218153 reaction equation
[C:1]([NH:5][C:6]([NH:8][CH2:9][C:10]([CH3:32])([CH3:31])[CH:11]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[N:19]=[CH:18]2)[CH2:12][CH:13]=[CH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].B1C2CCCC1CCC2.[OH-:42].[Na+].OO>C1COCC1.O>[C:1]([NH:5][C:6]([NH:8][CH2:9][C:10]([CH3:32])([CH3:31])[CH:11]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[N:19]=[CH:18]2)[CH2:12][CH2:13][CH2:14][OH:42])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 59251060HCID 59251060, compound

Product 1

HCID 59251071HCID 59251071, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-tert-butyl-3-(3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethylhex-5-enyl)urea (5.0 mg, 0.01 mmol) in anhydrous THF (2 mL) at 0 C was added 9-BBN (50 μL, 0.02 mmol) under nitrogen. Allowed reaction mixture to warm to RT and stirred overnight then added 10% NaOH solution (0.2 mL) and 30% H2O2 (1 mL). and stirred for 10 min. The reaction mixture was poured into a water (4 mL), extracted with ethyl acetate (2×10 mL), dried (Na2SO4) and purified by chromatography to give 3.2 mg (50% yield) of 1-tert-butyl-3-(3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-6-hydroxy-2,2-dimethylhexyl)urea. MS found: (M+H)+=455.

Workup

  1. stirringand stirred for 10 min
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. dry with materialdried (Na2SO4)
  4. custompurified by chromatography

Sources & evidence

ORD record
ord-a46be95aaa924923a959ca327831a161
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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