1-(5-Trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine trifluoroacetate → 4-Isopropoxy-3-[4-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine-1-carbonyl]-benzonitrile

HRID 1352409Notes

Reaction equation

HRID 1352409 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH:13]([CH3:15])[CH3:14])=[C:7]([CH:11]=1)[C:8]([OH:10])=O)#[N:2].FC(F)(F)C(O)=O.[F:23][C:24]([F:37])([F:36])[C:25]1[S:29][C:28]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[N:27][N:26]=1>>[CH:13]([O:12][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:11][C:7]=1[C:8]([N:33]1[CH2:32][CH2:31][N:30]([C:28]2[S:29][C:25]([C:24]([F:36])([F:23])[F:37])=[N:26][N:27]=2)[CH2:35][CH2:34]1)=[O:10])([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 211001991-(5-Trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine trifluoroacetateHCID 211002975-Cyano-2-isopropoxybenzoic acid

Product 1

HCID 211002964-Isopropoxy-3-[4-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine-1-carbonyl]-benzonitrileYield 80%

Procedure

Prepared in analogy to example 1 (b) from 5-cyano-2-isopropoxy-benzoic acid (Example A28) 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 80%). MS (m/e): 426.0 (M+H+, 100%).

Workup

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

Sources & evidence

ORD record
ord-26398b7756fd4b3fb3d76a7f08e9ab69
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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