3-[(4-Chloro-benzyl)-(1-methyl-1H-pyrazole-3-sulfonyl)-amino]-benzoic acid tert-butyl ester → 3-[(4-Chloro-benzyl)-(1-methyl-1H-pyrazole-3-sulfonyl)-amino]-benzoic acid

HRID 62813Notes

Reaction equation

HRID 62813 reaction equation
C([O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[S:14]([C:17]2[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=2)(=[O:16])=[O:15])[CH:8]=1)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:13]([S:14]([C:17]2[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=2)(=[O:15])=[O:16])[C:9]2[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=2)[C:6]([OH:31])=[O:5])=[CH:29][CH:28]=1

Participants

3

Reactant 1

HCID 673195783-[(4-Chloro-benzyl)-(1-methyl-1H-pyrazole-3-sulfonyl)-amino]-benzoic acid tert-butyl ester

Product 1

HCID 673194383-[(4-Chloro-benzyl)-(1-methyl-1H-pyrazole-3-sulfonyl)-amino]-benzoic acidYield 16.9%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 3-[(4-chloro-benzyl)-(1-methyl-1H-pyrazole-3-sulfonyl)-amino]-benzoic acid tert-butyl ester (1.33 g, 0.02 mol) in a mixture of trifluoroacetic acid/dichloromethane (20 ml, 1:1 v/v) was stirred for 3 hrs. The reaction mixture was concentrated to dryness in vacuo to afford the title compound as a white solid (1.37 g). HPLC retention time 2.75 Mass spectrum (ES+) m/z 405.9 (M+).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-c364baf3163246a1959e27d6e80f9bc3
Source dataset
uspto-grants-2016_09
Patent number
US09447033B2

Reaction notes

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