m-Chloroperbenzoic acid → (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-{[(4-propyl-4H-1,2,4-triazol-3-yl)methyl]sulfinyl}phenyl)acrylamide

HRID 30710Notes

Reaction equation

HRID 30710 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([S:25][CH2:26][C:27]3[N:31]([CH2:32][CH2:33][CH3:34])[CH:30]=[N:29][N:28]=3)=[CH:21][CH:20]=2)=[O:17])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:43])C=1>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH2:26][C:27]3[N:31]([CH2:32][CH2:33][CH3:34])[CH:30]=[N:29][N:28]=3)=[O:43])=[CH:21][CH:20]=2)=[O:17])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69206966(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-([(4-propyl-4H-1,2,4-triazol-3-yl)methyl]thio)phenyl)acrylamide

Product 1

HCID 69210641(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-{[(4-propyl-4H-1,2,4-triazol-3-yl)methyl]sulfinyl}phenyl)acrylamideYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-{[(4-propyl-4H-1,2,4-triazol-3-yl)methyl]thio}phenyl)acrylamide (96 mg), m-chloroperbenzoic acid (40 mg) and tetrahydrofuran (3 ml) was stirred at room temperature for 3 hrs. The reaction mixture was concentrated and purified by HPLC to give (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-{[(4-propyl-4H-1,2,4-triazol-3-yl)methyl]sulfinyl}phenyl)acrylamide (36 mg, 37%) as pale-yellow crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-9fe1ff0db4764ed981659acfd2c40b42
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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