Potassium Carbonate → 2-[5-Amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-sulfamoylphenyl)acetamide

HRID 551347Notes

Reaction equation

HRID 551347 reaction equation
[NH2:1][C:2]1[N:3]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH:18]3[CH2:20][CH2:19]3)=[CH:10][CH:9]=2)[C:4]([SH:7])=[N:5][N:6]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](=[O:41])(=[O:40])[NH2:39])=[CH:34][C:33]=1[Cl:42])=[O:30]>CN(C=O)C>[NH2:1][C:2]1[N:3]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH:18]3[CH2:20][CH2:19]3)=[CH:10][CH:9]=2)[C:4]([S:7][CH2:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([S:38](=[O:41])(=[O:40])[NH2:39])=[CH:34][C:33]=2[Cl:42])=[O:30])=[N:5][N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 215288302-chloro-N-(2-chloro-4-sulfamoylphenyl)acetamideHCID 178509206HCID 178509206, compound

Product 1

HCID 597636572-[5-Amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-sulfamoylphenyl)acetamideYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a solution of 5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-[1,2,4]triazole-3-thiol (708 mg, 2.5 mmol), K2CO3 (380 mg, 2.5 mmol) in DMF (20 mL) was added 2-chloro-N-(2-chloro-4-sulfamoylphenyl)acetamide (710 mg, 2.5 mmol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was evaporated. The residue was purified by silica gel chromatography to yield 2-[5-Amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-sulfamoylphenyl)acetamide (1.26 g, 95%).

Workup

  1. customUpon completion of the reaction
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-aed103002bc840b38eea5549c9d6e01a
Source dataset
uspto-grants-2011_05
Patent number
US07947721B2

Reaction notes

Loading…