Reaction #71674

Reaction equation

2-methyl-3-pyridinecarboxylic acid

HATU

DIPEA

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

→

title compound

Yield 98.0%

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

Yield 98.0%

Solvents

DCM

DMF

Conditions

Workup

1. 1
   Concentrationthe reaction mixture was then concentrated
2. 2
   Otherpurified by reverse phase MDAP
3. 3
   ConcentrationThe collected fractions were concentrated in vacuo

Procedure

To a solution of 2-methyl-3-pyridinecarboxylic acid (47.7 mg, 0.348 mmol) in DCM (2.000 ml) was added HATU (132 mg, 0.348 mmol) and DIPEA (0.152 ml, 0.870 mmol) and the mixture stirred for 15 minutes before addition of (2R)-2-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine hydrochloride (Description 6) (100 mg, 0.290 mmol) in DMF (2 ml). The resultant mixture was stirred for 16 h at room temperature then the reaction mixture was then concentrated and the residue taken up in DMSO and purified by reverse phase MDAP. The collected fractions were concentrated in vacuo giving the title compound (80.7 mg) as a white solid.

Source