1-(5-Trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine trifluoroacetate → [5-Methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-phenyl]-[4-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazin-1-yl]-methanone

HRID 1352415Notes

Reaction equation

HRID 1352415 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][CH2:15][C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])=[C:9]([CH:13]=1)[C:10](O)=[O:11])(=[O:4])=[O:3].FC(F)(F)C(O)=O.[F:30][C:31]([F:44])([F:43])[C:32]1[S:36][C:35]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[N:34][N:33]=1>>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][CH2:15][C:16]([F:22])([F:21])[C:17]([F:19])([F:20])[F:18])=[C:9]([C:10]([N:40]2[CH2:39][CH2:38][N:37]([C:35]3[S:36][C:32]([C:31]([F:43])([F:30])[F:44])=[N:33][N:34]=3)[CH2:42][CH2:41]2)=[O:11])[CH:13]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 211001991-(5-Trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine trifluoroacetateHCID 211003155-Methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-benzoic acid

Product 1

HCID 21100316[5-Methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-phenyl]-[4-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazin-1-yl]-methanoneYield 56%

Procedure

Prepared in analogy to example 1 (b) from 5-methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-benzoic acid (Example A30) and 1-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine trifluoroacetate (Example 62(b)). The crude material was purified by chromatography (SiO2, methanol/dichloromethane) to yield the title compound as an off-white solid (yield 56%). MS (m/e): 569.3 (M+H+, 100%).

Workup

  1. customThe crude material was purified by chromatography (SiO2, methanol/dichloromethane)

Sources & evidence

ORD record
ord-1a8dd43b1f5c472ca889534a5bc61157
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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