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 592519Notes

Reaction equation

HRID 592519 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 101i (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 101j (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-8e6ddb8c768840fdb0239b96c3cf1006
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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