Phosgene → 4-(4-Acryloylamino-benzenesulfonyl)-piperazine-1-carboxylic acid 2-chloro-benzyl ester

Phosgene (0.5 ml, 20% solution in toluene) was added in one portion to a stirred solution of 2-chlorobenzyl alcohol (0.1 g, 0.7 mmol) in THF (2 ml) and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the reaction mixture was concentrated under vacuum and the resulting residue was diluted with DMF (2 ml) and added drop wise to a stirred solution of N-[4-(piperazine-1-sulfonyl)-phenyl]-acrylamide (0.16 g, 0.54 mmol) and diisopropylethylamine (0.19 ml, 1.1 mmol) in DMF (4 ml). The resulting mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours. After this time the reaction mixture was concentrated under vacuum and the residue was purified by Prep HPLC to give the title compound (0.029 g, 12% yield) as a white powder.

1. concentrationAfter this time the reaction mixture was concentrated under vacuum
2. additionthe resulting residue was diluted with DMF (2 ml)
3. stirringThe resulting mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours
4. concentrationAfter this time the reaction mixture was concentrated under vacuum
5. customthe residue was purified by Prep HPLC

ORD record

ord-852b23af1f314c938a12cbf4ce4c30bc

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946197B2