1-(5-Trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine trifluoroacetate → 4-Cyclopentyloxy-N-methyl-3-[4-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine-1-carbonyl]-benzenesulfonamide

HRID 1352414Notes

Reaction equation

HRID 1352414 reaction equation
[CH:1]1([O:6][C:7]2[CH:15]=[CH:14][C:13]([S:16](=[O:20])(=[O:19])[NH:17][CH3:18])=[CH:12][C:8]=2[C:9]([OH:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[F:28][C:29]([F:42])([F:41])[C:30]1[S:34][C:33]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[N:32][N:31]=1>>[CH:1]1([O:6][C:7]2[CH:15]=[CH:14][C:13]([S:16]([NH:17][CH3:18])(=[O:20])=[O:19])=[CH:12][C:8]=2[C:9]([N:38]2[CH2:37][CH2:36][N:35]([C:33]3[S:34][C:30]([C:29]([F:41])([F:28])[F:42])=[N:31][N:32]=3)[CH2:40][CH2:39]2)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 211001991-(5-Trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine trifluoroacetateHCID 21100227HCID 21100227, compound

Product 1

HCID 211001644-Cyclopentyloxy-N-methyl-3-[4-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine-1-carbonyl]-benzenesulfonamideYield 46%

Procedure

Prepared in analogy to example 1 (b) from 2-cyclopentyloxy-5-methylsulfamoyl-benzoic acid (Example A29) and 1-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine trifluoroacetate (Example 62(b)). The crude material was purified by chromatography (SiO2, ethyl acetate/heptane) to yield the title compound as a white solid (yield 46%). MS (m/e): 520.3 (M+H+, 100%).

Workup

  1. customThe crude material was purified by chromatography (SiO2, ethyl acetate/heptane)

Sources & evidence

ORD record
ord-e91f1bcaf5804de68c563ca994cb95fb
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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