1-Methylpiperazine → N-(4-chloro-3-(pyridin-2-yl)phenyl)-6-((4-methylpiperazin-1-yl)methyl)pyridine-3-carboxamide

HRID 922844Notes

Reaction equation

HRID 922844 reaction equation
Br[CH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:13]=2)=[O:10])=[CH:5][CH:4]=1.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>CS(C)=O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:9]([C:6]2[CH:7]=[N:8][C:3]([CH2:2][N:29]3[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]3)=[CH:4][CH:5]=2)=[O:10])=[CH:13][C:14]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 668776406-(bromomethyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)pyridine-3-carboxamide

Product 1

HCID 44252150N-(4-chloro-3-(pyridin-2-yl)phenyl)-6-((4-methylpiperazin-1-yl)methyl)pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-(bromomethyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)pyridine-3-carboxamide was dissolved in 1 mL of DMSO and stirred for 1 h with N-methylpiperazine. The reaction was concentrated, and the crude residue was purified by reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-6-((4-methylpiperazin-1-yl)methyl)pyridine-3-carboxamide as a pure product. MS (Q1) 422.3 (M)+.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe crude residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-4b3256c1624f4be09cced2a3634f5142
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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