Hydrogen Peroxide → HCID 59375044, compound

HRID 661945Notes

Reaction equation

HRID 661945 reaction equation
C([C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[C:8]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N:25]5[CH2:33][C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[C:26]5=[O:34])[C:20]=4[CH3:35])=[CH:9][CH:10]=[C:11]([C:16]([NH2:18])=[O:17])[C:12]=3[NH:13]2)=[CH:5][CH:4]=1)=O.S(=O)(=O)(O)[OH:37].OO.[OH-].[Na+]>CO.O>[OH:37][C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[C:8]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N:25]5[CH2:33][C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[C:26]5=[O:34])[C:20]=4[CH3:35])=[CH:9][CH:10]=[C:11]([C:16]([NH2:18])=[O:17])[C:12]=3[NH:13]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 86642955HCID 86642955, compound

Product 1

HCID 59375044HCID 59375044, compoundYield 15.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Step 3 A suspension of 7-formyl-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide (30 mg, 0.052 mmol) in methanol (1 mL) was treated with sulfuric acid (4.2 mL, 0.078 mmol) followed by 30% aqueous hydrogen peroxide (0.032 mL, 0.313 mmol), and stirred at rt for 23 h, The mixture was treated with 1 M aqueous sodium hydroxide (200 mL) and stirred for 1 h. The mixture was diluted with water and the precipitate was collected by filtration, washed with water and dried. The residue was purified by preparative HPLC to provide 7-hydroxy-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide as a tan powder (3.6 mg, 15%). 1H NMR (400 MHz, methanol-d4) δ 7.90 (1H, d, J=7.5 Hz), 7.86 (1H, d, J=7.9 Hz), 7.65-7.76 (2H, m), 7.48-7.63 (3H, m), 7.42 (1H, d, J=6.6 Hz), 7.03 (1H, d, J=7.9 Hz), 6.98 (1H, s), 6.92 (1H, d, J=8.8 Hz), 6.54 (1H, d, J=9.0 Hz), 4.97 (2H, s), 1.94 (3H, s). Mass spectrum m/z 448.1 (M+H)+.

Workup

  1. stirringstirred for 1 h
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-0302574f5e304ee390464daf7ea30d46
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

Loading…