tert-Butyl 8-(6-(5-Bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate → 3-(5-(3,8-Diazabicyclo[3.2.1]octan-8-yl)pyridin-2-ylamino)-5-bromo-1-methyl-pyridin-2(1H)-one

HRID 1411629Notes

Reaction equation

HRID 1411629 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[CH:22]4[CH2:23][CH2:24][CH:18]3[CH2:19][N:20](C(OC(C)(C)C)=O)[CH2:21]4)=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1>Cl.O1CCOCC1>[CH:18]12[N:17]([C:14]3[CH:13]=[CH:12][C:11]([NH:10][C:4]4[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=[C:2]([Br:1])[CH:3]=4)=[N:16][CH:15]=3)[CH:22]([CH2:23][CH2:24]1)[CH2:21][NH:20][CH2:19]2

Participants

3

Reactant 1

HCID 86684267tert-Butyl 8-(6-(5-Bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate

Product 1

HCID 866842683-(5-(3,8-Diazabicyclo[3.2.1]octan-8-yl)pyridin-2-ylamino)-5-bromo-1-methyl-pyridin-2(1H)-oneYield 98%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A mixture of 152c (900 mg, 1.84 mmol) and 4.0M HCl/dioxane (60 mL) was stirred at room temperature for 5 h. It was then concentrated under reduced pressure to afford crude 152d as a yellow solid (700 mg, 98%), which was used in the next step without further purification. MS-ESI: [M+H]+ 390.3.

Workup

  1. concentrationIt was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-6920c98bca6542c4a02427b1836c0a91
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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