Reaction #71676

Reaction equation

HBTU

(2S)-2-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine hydrochloride

HOBT

DIPEA

2-methyl-3-pyridinecarboxylic acid

H2O

→

title compound

Yield 87.0%

(2S)-2-Methyl-4-[(2-methyl-3-pyridinyl)carbonyl]-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine formic acid salt

Yield 87.0%

Solvents

THF

Conditions

Workup

1. 1
   ConcentrationThe mixture was then concentrated
2. 2
   Otherthe residue partitioned between DCM (10 ml) and water (10 ml)
3. 3
   Otherthe layers were separated
4. 4
   Concentrationthe organic layers concentrated to dryness
5. 5
   workup.DISSOLUTIONthe crude dissolved in DMSO
6. 6
   Otherpurified by MDAP

Procedure

To a solution of (2S)-2-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine hydrochloride (Description 8) (100 mg, 0.270 mmol) in THF (5 ml) was added HOBT.H2O (41.3 mg, 0.270 mmol), HBTU (102 mg, 0.270 mmol) and 2-methyl-3-pyridinecarboxylic acid (40.7 mg, 0.297 mmol). The mixture was stirred for 5 min before addition of DIPEA (0.118 ml, 0.674 mmol) and the resultant solution stirred at room temperature for 16 h. The mixture was then concentrated and the residue partitioned between DCM (10 ml) and water (10 ml), the layers were separated using a hydrophobic frit and the organic layers concentrated to dryness and the crude dissolved in DMSO and purified by MDAP giving the title compound (61.2 mg) as a white solid.

Source