Tert-butyl 3-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)azetidine-1-carboxylate → 3-(5-(azetidin-3-yl)pyridin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one

HRID 592963Notes

Reaction equation

HRID 592963 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[CH:15][C:14]([CH:17]3[CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]3)=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1>Cl.O1CCOCC1>[NH:19]1[CH2:20][CH:17]([C:14]2[CH:13]=[CH:12][C:11]([NH:10][C:4]3[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=[C:2]([Br:1])[CH:3]=3)=[N:16][CH:15]=2)[CH2:18]1

Participants

3

Reactant 1

HCID 58044058Tert-butyl 3-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)azetidine-1-carboxylate

Product 1

HCID 580437193-(5-(azetidin-3-yl)pyridin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-oneYield 84.3%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

Compound 239a (1.0 g, 2.3 mmol) was suspended in 4M HCl/dioxane (10 mL). The reaction mixture was stirred at room temperature for 4 h. It was then concentrated under reduced pressure. The residue was basified with aqueous NaOH and the resulting mixture was extracted with dichloromethane. The combined organic layer was washed with brine and concentrated under reduced pressure to afford 239b as a yellow solid (650 mg, 84%). MS-ESI: [M+H]+ 335.

Workup

  1. concentrationIt was then concentrated under reduced pressure
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. washThe combined organic layer was washed with brine
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1e47ea2bd5634f65bef614a93067b0a4
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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