5-Isopropyl-1,3,4-thiadiazol-2-amine → N-{2-[4-(5-Isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-acetamide

HRID 2266395Notes

Reaction equation

[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[CH:17]([C:20]1[S:24][C:23]([NH2:25])=[N:22][N:21]=1)([CH3:19])[CH3:18]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH:17]([C:20]1[S:24][C:23]([NH:25][S:13]([C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])=[CH:8][CH:9]=2)(=[O:15])=[O:14])=[N:22][N:21]=1)([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 60 °C

Procedure

22.0 g 4-(2-Acetylamino-ethyl)-benzenesulfonyl chloride, 12.0 g 5-isopropyl-[1,3,4]thiadiazol-2-yl-amine and 1.0 g 4-dimethylaminopyridine were dissolved in 300 ml pyridine and stirred at 60° C. for thirty minutes. The pyridine was removed in vacuo and the residue coevaporated three times with portions of 100 ml toluene. The residue was purified by chromatography on silica gel with the eluents dichloromethane:methanol=95:5 to obtain 16.8 g N-{2-[4-(5-Isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-acetamide as a solid.

Workup

customThe pyridine was removed in vacuo
customThe residue was purified by chromatography on silica gel with the eluents dichloromethane

Sources & evidence

ORD record: ord-5ef034faae024da4ae3d5b6540c2aa60
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858647B2

Reaction notes

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