5-Bromo-1-methyl-3-((5-(morpholine-4-carbonyl)pyridin-2-yl)amino)pyridin-2(1H)-one → 5-Bromo-1-methyl-3-(5-morpholin-4-ylmethyl-pyridin-2-ylamino)-1H-pyridin-2-one

HRID 68443Notes

Reaction equation

HRID 68443 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=O)=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

3

Reactant 1

HCID 576627795-Bromo-1-methyl-3-((5-(morpholine-4-carbonyl)pyridin-2-yl)amino)pyridin-2(1H)-one

Product 1

HCID 592165315-Bromo-1-methyl-3-(5-morpholin-4-ylmethyl-pyridin-2-ylamino)-1H-pyridin-2-oneYield 22.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-1-methyl-3-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-1H-pyridin-2-one (2.3 g, 5.9 mmol) was dissolved in 30 mL tetrahydrofuran. Borane tetrahydrofuran complex (2.5 g, 29 mmol) was added. After stirring for 18 hours, this was concentrated in vacuo. Ethanol was added. This was refluxed for one hour. This was concentrated in vacuo and purified by flash chromatography to yield 5-Bromo-1-methyl-3-(5-morpholin-4-ylmethyl-pyridin-2-ylamino)-1H-pyridin-2-one (500 mg, 1.32 mmol). MS (ESI) 381.0 (M+H)+.

Workup

  1. additionBorane tetrahydrofuran complex (2.5 g, 29 mmol) was added
  2. concentrationthis was concentrated in vacuo
  3. additionEthanol was added
  4. temperatureThis was refluxed for one hour
  5. concentrationThis was concentrated in vacuo
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e8dc1bc4d12f44319202bd8bf8d087e0
Source dataset
uspto-grants-2014_09
Patent number
US08822457B2

Reaction notes

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