1,4-Dioxane hydrochloride → 5-Bromo-1-methyl-3-(6-(piperazin-1-yl)pyridin-3-ylamino)-pyrazin-2(1H)-one

HRID 592834Notes

Reaction equation

HRID 592834 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([N:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[N:13][CH:14]=2)[C:5](=[O:28])[N:4]([CH3:29])[CH:3]=1.Cl.O1CCOCC1>ClCCl>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[N:13][C:12]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[C:5](=[O:28])[N:4]([CH3:29])[CH:3]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86684363tert-Butyl 4-(5-(6-Bromo-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 866843645-Bromo-1-methyl-3-(6-(piperazin-1-yl)pyridin-3-ylamino)-pyrazin-2(1H)-oneYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 197c (500 mg, 1.08 mmol) in dichloromethane (10 mL) was added 4.0 M HCl/dioxane (10 mL). The reaction mixture was stirred at room temperature for 5 h. It was then concentrated under reduced pressure to afford 197d (358 mg, 91%). MS-ESI: [M+H]+ 365.

Workup

  1. concentrationIt was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-ae4ed488832b4818b7ab8f7431be691c
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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