Hydrogen Peroxide → HCID 178488662, compound

HRID 82756Notes

Reaction equation

HRID 82756 reaction equation
[NH:1]1[C:5]([CH2:6][CH2:7][N:8]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[C:9]2[C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][C:22]=2[CH3:29])=[N:4][N:3]=[N:2]1.[OH-:30].[Na+].OO>CS(C)=O.O>[NH:4]1[C:5]([CH2:6][CH2:7][N:8]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)=[C:9]2[C:21]2[CH:28]=[CH:27][C:24]([C:25]([NH2:26])=[O:30])=[CH:23][C:22]=2[CH3:29])=[N:1][N:2]=[N:3]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 178488661HCID 178488661, compound

Product 1

HCID 178488662HCID 178488662, compoundYield 9.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 4-(1-(2-(1H-tetrazol-5-yl)ethyl)-3-(4-methoxyphenyl)-1H-pyrrol-2-yl)-3-methylbenzonitrile (9J, R=2-(1H-tetrazol-5-yl)ethyl) (250 mg, 0.65 mmol) in DMSO (5 mL) was added a solution of NaOH (52 mg, 1.3 mmol) in a mixture of water (0.5 mL) and H2O2 (74 mg, 0.65 mmol). After being stirred at room temperature for 4 hours, the mixture was purified by preparative HPLC to give 24 mg of 4-(1-(2-(1H-tetrazol-5-yl)ethyl)-3-(4-methoxyphenyl)-1H-pyrrol-2-yl)-3-methylbenzamide (9K, R=2-(1H-tetrazol-5-yl)ethyl) (yield 9% in two steps) as a grey solid.

Workup

  1. customthe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-db5ece2b503e45d4b56b88e01162604e
Source dataset
uspto-grants-2014_09
Patent number
US08846736B2

Reaction notes

Loading…