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 1916058Notes

Reaction equation

HRID 1916058 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-3e32b7c6ce2b48be80bd59f7aef6b91f
Source dataset
uspto-grants-2013_12
Patent number
US08618098B2

Reaction notes

Loading…