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

HRID 1820707Notes

Reaction equation

HRID 1820707 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][C:6]=1[C:7]([OH:9])=O)([CH3:3])[CH3:2].[F:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CO.C(O)=O>[F:18][C:19]1[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[CH:21][C:20]=1[N:29]1[CH2:34][CH2:33][N:32]([C:7]([C:6]2[CH:10]=[C:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:12]=[CH:13][C:5]=2[O:4][CH:1]([CH3:2])[CH3:3])=[O:9])[CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 211002372-Isopropoxy-5-methylsulfonylbenzoic acid2×HCID 468374951-(2-Fluoro-4-(trifluoromethyl)phenyl)piperazine

Product 1

HCID 11352274[4-(2-Fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18963719Formic acid methanolSolvent

Procedure

A mixture of 0.05 mmol 2-isopropoxy-5-methanesulfonyl-benzoic acid (Compound 1.2), 0.06 mmol 1-(2-fluoro-4-trifluoromethyl-phenyl)-piperazine, 0.055 mmol TBTU and 0.25 mmol DIPEA in 1 ml DMF was stirred at RT for 16 h. 0.5 ml MeOH/HCOOH 1/1 was added and the mixture was subjected to reversed phase preparative HPLC separation eluting with an acetonitrile/water gradient yielding the title compound.

Workup

  1. customthe mixture was subjected to reversed phase preparative HPLC separation
  2. washeluting with an acetonitrile/water

Sources & evidence

ORD record
ord-c7285773228b4331a4918b6b8d4aba20
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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