Reaction #1256777

Reaction equation

methanesulfonyl chloride

CH2Cl2

1-(2-chloro-5-(piperazin-1-ylmethyl)benzyl)-3-(6-methylpyridin-3-yl)urea hydrochloride salt

DIPEA

→

1-(2-chloro-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)benzyl)-3-(6-methylpyridin-3-yl)urea

Solvents

EtOAc

Conditions

Workup

1. 1
   OtherIn a 20 mL scintillation vial equipped with a stir bar
2. 2
   Othercap
3. 3
   Temperaturemaintained under a positive nitrogen pressure
4. 4
   WashThe organic solution was washed with 4 mL each of water and saturated NaCl solution
5. 5
   Dryingdried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated

Procedure

In a 20 mL scintillation vial equipped with a stir bar, 1-(2-chloro-5-(piperazin-1-ylmethyl)benzyl)-3-(6-methylpyridin-3-yl)urea hydrochloride salt (367 mg, 654 □mol) and DMAP (2 mg) were sealed with a septum cap and maintained under a positive nitrogen pressure. To the mixture was added 6 mL of anyhydrous CH2Cl2, followed by DIPEA (520 □L, 2.94 mmol) and methanesulfonyl chloride (70 □L, 785 □mol). The reaction mixture was stirred for 16 h. The reaction mixture was diluted with 6 mL of EtOAc. The organic solution was washed with 4 mL each of water and saturated NaCl solution, dried over Na2SO4, filtered and concentrated to afford 1-(2-chloro-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)benzyl)-3-(6-methylpyridin-3-yl)urea as beige foam (209 mg).

Source