Reaction #71684

Reaction equation

H2O

HBTU

DIPEA

(3R)-3-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

2-methyl-3-pyridinecarboxylic acid

HOBT

→

title compound

Yield 122.3%

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

Yield 122.3%

Solvents

DMF

Conditions

Workup

1. 1
   OtherThe DMF was evaporated under vacuum, 5 ml of DCM
2. 2
   workup.ADDITIONadded
3. 3
   Washwashed with saturated NaHCO3 solution (5 ml)
4. 4
   Otherdried on a phase separation cartridge
5. 5
   Otherevaporated under vacuo
6. 6
   workup.DISSOLUTIONThe crude material was dissolved in MeCN/DMSO 1:1
7. 7
   Otherpurified by MDAP

Procedure

To a solution of (3R)-3-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (Description 12) (80 mg, 0.259 mmol) in DMF (4 ml) was added 2-methyl-3-pyridinecarboxylic acid (35.6 mg, 0.259 mmol), HOBT.H2O (39.7 mg, 0.259 mmol), HBTU (98 mg, 0.259 mmol) and DIPEA (0.136 ml, 0.778 mmol) and the reaction mixture was stirred at room temperature for 1 h. The DMF was evaporated under vacuum, 5 ml of DCM added and then washed with saturated NaHCO3 solution (5 ml), dried on a phase separation cartridge and evaporated under vacuo. The crude material was dissolved in MeCN/DMSO 1:1 and purified by MDAP to give the title compound (75 mg).

Source