Hydrogen Peroxide → HCID 25061489, compound

HRID 2244078Notes

Reaction equation

HRID 2244078 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]3[C:20]4[CH2:19][C:18]([CH3:22])([CH3:21])[CH2:17][C:16](=[O:23])[C:15]=4[C:14]([CH3:24])=[CH:13]3)=[CH:9][CH:10]=2)[C:5]([C:25]#[N:26])=[CH:4][N:3]=1.[OH-:27].[Na+].OO.O>CCO.CS(C)=O>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]3[C:20]4[CH2:19][C:18]([CH3:21])([CH3:22])[CH2:17][C:16](=[O:23])[C:15]=4[C:14]([CH3:24])=[CH:13]3)=[CH:9][CH:10]=2)[C:5]([C:25]([NH2:26])=[O:27])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 25061240HCID 25061240, compound

Product 1

HCID 25061489HCID 25061489, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 22338741Dimethylsulfoxide ethanolSolvent

Procedure

A suspension of 1-amino-6-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indol-1-yl)-isoquinoline-4-carbonitrile (0.066 g, 0.19 mmol) in EtOH/DMSO (3:1, 2 mL) is treated with an aqueous solution of NaOH (1 M, 0.03 mL) and H2O2 (30%, 0.1 mL). The reaction mixture is stirred at RT for 2 h. The reaction mixture is treated with H2O (20 mL). The aqueous phase is extracted with EtOAc (2×). The combined organic layers are dried over MgSO4. The solvent is evaporated and the residue is dried under vacuum. Purification of the crude material using a Biotage column (0-20% MeOH/CH2Cl2) affords 0.02 g (29%) of 1-amino-6-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indol-1-yl)-isoquinoline-4-carboxylic acid amide. LC/MS m/z=363 [M+H]+, RT=1.93 min.

Workup

  1. extractionThe aqueous phase is extracted with EtOAc (2×)
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. customThe solvent is evaporated
  4. customthe residue is dried under vacuum
  5. customPurification of the crude material

Sources & evidence

ORD record
ord-5b588bcc52f0420bae55aa77746cae76
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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