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

HRID 1518987Notes

Reaction equation

HRID 1518987 reaction equation
[C:1]([O:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:23][N:24]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[N:25]1.N1C=CC=CC=1.O>ClCCl>[C:1]([O:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[S:29]([C:26]2[CH:27]=[CH:28][N:24]([CH3:23])[N:25]=2)(=[O:31])=[O:30])[CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 134744661-Methyl-1H-pyrazole-3-sulfonyl chlorideHCID 673094663-(4-Chloro-benzylamino)-benzoic acid tert-butyl ester

Product 1

HCID 673195783-[(4-Chloro-benzyl)-(1-methyl-1H-pyrazole-3-sulfonyl)-amino]-benzoic acid tert-butyl esterYield 9.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(4-chloro-benzylamino)-benzoic acid tert-butyl ester (1 g, 0.03 mol), 1-Methyl-1H-Pyrazole-3-sulfonyl chloride (1.13 g, 0.06 mol) and pyridine (0.5 ml 0.06 mol) in dichloromethane (40 ml) were refluxed for 48 hrs. On cooling, water (50 ml) was added with stirring, the organic layer was separated, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/dichloromethane 0% to 10% v/v) to afford the title compound as a clear oil (1.33 g). Mass spectrum (ES+) m/z 49 (M+H).

Workup

  1. temperatureOn cooling
  2. customthe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (ethyl acetate/dichloromethane 0% to 10% v/v)

Sources & evidence

ORD record
ord-e89dfcb542444905b11e8305f10511fb
Source dataset
uspto-grants-2015_07
Patent number
US09073834B2

Reaction notes

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