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

HRID 1798960Notes

Reaction equation

HRID 1798960 reaction equation
[C:1]([NH:4][C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1)(=[O:3])[CH3:2].[CH:20]([C:23]1[S:27][C:26]([NH2:28])=[N:25][N:24]=1)([CH3:22])[CH3:21]>N1C=CC=CC=1>[CH:20]([C:23]1[S:27][C:26]([NH:28][S:16]([C:13]2[CH:14]=[CH:15][C:10]([C@@H:6]3[CH2:7][CH2:8][CH2:9][C@H:5]3[NH:4][C:1](=[O:3])[CH3:2])=[CH:11][CH:12]=2)(=[O:18])=[O:17])=[N:25][N:24]=1)([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 1471515-Isopropyl-1,3,4-thiadiazol-2-amineHCID 58433496Trans-4-(2-acetylamino-cyclopentyl)-benzenesulfonyl chloride

Product 1

HCID 58433495Trans-N-{2-[4-(5-isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-cyclopentyl}-acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

608 mg of trans-4-(2-acetylamino-cyclopentyl)-benzenesulfonyl chloride, 3 ml of pyridine and 286 mg of 5-Isopropyl-1,3,4-thiadiazol-2-ylamine were stirred at room temperature for 30 minutes. The solvent was evaporated, the residue was treated with 20 ml 2n hydrochloric acid and the product extracted with 30 ml ethyl acetate and purified by column chromatography (silca gel, DCM:methanol=96:4).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was treated with 20 ml 2n hydrochloric acid
  3. extractionthe product extracted with 30 ml ethyl acetate
  4. custompurified by column chromatography (silca gel, DCM:methanol=96:4)

Sources & evidence

ORD record
ord-5bf8270e08f84b399d6828c9532c7640
Source dataset
uspto-grants-2013_01
Patent number
US08344004B2

Reaction notes

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