Chloroacetic Acid → HCID 67322178, compound

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[C:5]([NH:7][C:8]1[C:9]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1)=[O:6].Cl[CH2:25][C:26]([OH:28])=[O:27]>CN(C)C=O.O>[Cl:14][C:12]1[CH:13]=[C:8]([NH:7][C:5](=[O:6])[C:4]2[CH:21]=[CH:22][CH:23]=[C:2]([Cl:1])[CH:3]=2)[C:9]([N:15]2[CH2:20][CH2:19][N:18]([CH2:25][C:26]([OH:28])=[O:27])[CH2:17][CH2:16]2)=[N:10][CH:11]=1

Participants

Procedure

A mixture of 0.100 g (0.285 mmol) of 3-chloro-N-(5-chloro-2-piperazin-1-yl-pyridin-3-yl)-benzamide and 0.040 g (0.43 mmol) of chloroacetic acid in N,N-dimethylformamide is stirred overnight at room temperature then heated to 100° C. for 24 hours. The mixture is cooled to room temperature, diluted with water, and extracted with ethyl acetate. The aqueous phase is concentrated under reduced pressure and the residue is purified by preparative reverse phase HPLC to provide 0.009 g (11%) of {4-[5-chloro-3-(3-chloro-benzoylamino)-pyridin-2-yl]-piperazin-1-yl}-acetic acid as a white solid.