Dimethyl Sulfoxide → 4-((4-acetylpiperazin-1-yl)methyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide

HRID 922845Notes

Reaction equation

HRID 922845 reaction equation
Br[CH2:2][C:3]1N=[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.[C:25]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)(=[O:27])[CH3:26].[CH3:34]S(C)=O>>[C:25]([N:28]1[CH2:33][CH2:32][N:31]([CH2:2][C:3]2[CH:34]=[CH:7][C:6]([C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[CH:13]=3)=[O:10])=[CH:5][CH:4]=2)[CH2:30][CH2:29]1)(=[O:27])[CH3:26]

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 837951-AcetylpiperazineHCID 668776406-(bromomethyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)pyridine-3-carboxamide

Product 1

HCID 442522944-((4-acetylpiperazin-1-yl)methyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide

Procedure

6-(bromomethyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)pyridine-3-carboxamide (85 mg) was dissolved in DMSO (1 mL) and stirred for 1 h with N-acetylpiperazine. The reaction mixture was concentrated, and the crude residue was purified by revered phase HPLC to yield 4-((4-acetylpiperazin-1-yl)methyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide. MS (Q1) 449.1 (M)+.

Workup

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

Sources & evidence

ORD record
ord-f4565d15b20044699112ea4d92afdfac
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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