1,2-Dichloroethane → 1-[5-(3-methanesulfonylamino-2-methoxy-5-trifluoromethyl-phenylcarbamoyl)-2-methyl-phenyl]-1H-1,2,3-triazole-4-carboxylic Acid Methyl Ester

Participants

Reaction Conditions

Reaction Steps

1-(5-Carboxy-2-methyl-phenyl)-1H-1,2,3-triazole-4-carboxylic acid methyl ester (26 mg, 0.101 mmol) was stirred with 21 mg (0.153 mmol) of 1-hydroxy-7-azabenzotriazole (HOAt) in 1 mL of DMF and 24 mg (0. 126 mmol) of EDC was added. After 1 h of stirring at about 10° C., 30 mg (0.106 mmol) of N-(3-amino-2-methoxy-5-trifluoromethyl-phenyl) -methanesulfonamide was added. The mixture was stirred overnight then heated to 60° C. for 6 h. The reaction was then cooled and water was added. The precipitate was collected and chromatographed twice by preparative TLC (5% MeOH in CH2Cl2) and once by flash chromatography (0-4.5% MeOH in dichloromethane). The pure fractions yielded 3 mg (5.6%) of the title compound. ESI MS (m/z 526, 100, M−H).

Provenance & Evidence