Tert-butyl 4-(6-((5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)amino)pyridin-3-yl)piperazine-1-carboxylate → 5-Bromo-1-methyl-3-((5-(piperazin-1-yl)-pyridin-2-yl)amino)pyridin-2(1H)-one

HRID 1918959Notes

Reaction equation

HRID 1918959 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1>Cl.O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:15][N:16]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

3

Reactant 1

HCID 58043929Tert-butyl 4-(6-((5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)amino)pyridin-3-yl)piperazine-1-carboxylate

Product 1

HCID 580436655-Bromo-1-methyl-3-((5-(piperazin-1-yl)-pyridin-2-yl)amino)pyridin-2(1H)-oneYield 87%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A mixture of 188c (3.6 g, 7.8 mmol) and 4.0 M HCl/dioxane (10 mL) was stirred for 5 h at room temperature. It was then concentrated at reduced pressure. The residue was basified with aqueous 1.0M NaOH and extracted with methylene chloride. The combined organic layers were washed with water and concentrated under reduced pressure to give 188d (2.46 g, 87%). MS: [M+H]+ 364.

Workup

  1. concentrationIt was then concentrated at reduced pressure
  2. extractionextracted with methylene chloride
  3. washThe combined organic layers were washed with water
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a6e586843bc4b7fbb21efca8ad500e1
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

Loading…