Chloroacetic Acid → HCID 67322178, compound

HRID 1846676Notes

Reaction equation

HRID 1846676 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

5

Reactant 2

HCID 300Chloroacetic AcidHCID 67323078HCID 67323078, compound

Product 1

HCID 67322178HCID 67322178, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

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.

Workup

  1. temperaturethen heated to 100° C. for 24 hours
  2. temperatureThe mixture is cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. concentrationThe aqueous phase is concentrated under reduced pressure
  5. customthe residue is purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-c4979ca620fc499f80226eb886c97c4e
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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