Diisopropylethylamine → (2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

HRID 2374255Notes

Reaction equation

HRID 2374255 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[F:46][C:47]([F:61])([F:60])[C:48]1[CH:53]=[CH:52][C:51]([N:54]2[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]2)=[CH:50][CH:49]=1>CN(C)C=O>[I:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([N:57]1[CH2:56][CH2:55][N:54]([C:51]2[CH:50]=[CH:49][C:48]([C:47]([F:60])([F:61])[F:46])=[CH:53][CH:52]=2)[CH2:59][CH2:58]1)=[O:6]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1217181-(4-(Trifluoromethyl)phenyl)piperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 574452812-Iodo-5-methanesulfonyl-benzoic acid

Product 1

HCID 59793691(2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-Iodo-5-methanesulfonyl-benzoic acid (Example C, 3.0 g, 9.2 mmol) in dimethylformamide (20 ml) were successively added TBTU (3.8 g, 11.5 mmol), N-ethyldiisopropylamine (8.0 ml, 46.0 mmol) and 1-(4-trifluromethylphenyl)piperazine (ABCR F07741NB, [30459-17-7], 2.5 g, 11.0 mmol). The reaction was then stirred at room temperature for two hours, then concentrated in vacuo and purified by column chromatography (SiO2, 50 g, CH2Cl2/MeOH/NH3=100/0/0 to 95/4.5/0.5), to give the title compound as a pale brown foam; MS (m/e): 539.1 (M+H+). TBTU=2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by column chromatography (SiO2, 50 g, CH2Cl2/MeOH/NH3=100/0/0 to 95/4.5/0.5)

Sources & evidence

ORD record
ord-8e962f6ac4364df28c57194238c02608
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

Loading…