Ethanol → 3-[5-(1-Amino-1-methyl-ethyl)-pyridin-2-ylamino]-5-bromo-1-methyl-1H-pyridin-2-one

HRID 2069864Notes

Reaction equation

HRID 2069864 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[CH:15][C:14]([C:17]([NH:20]C(=O)CCl)([CH3:19])[CH3:18])=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.NC(N)=S.C(O)C.C(=O)(O)[O-].[Na+]>O.C(O)(=O)C>[NH2:20][C:17]([C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:4]2[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=[C:2]([Br:1])[CH:3]=2)=[N:16][CH:15]=1)([CH3:18])[CH3:19]

Participants

7

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 59473779N-{1-[6-(5-Bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino)-pyridin-3-yl]-1-methyl-ethyl}-2-chloro-acetamide

Product 1

HCID 594738243-[5-(1-Amino-1-methyl-ethyl)-pyridin-2-ylamino]-5-bromo-1-methyl-1H-pyridin-2-oneYield 91%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

N-{1-[6-(5-Bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino)-pyridin-3-yl]-1-methyl-ethyl}-2-chloro-acetamide (2.97 g, 7.2 mmol) and thiourea (0.655 g, 8.6 mmol) were suspended in an ethanol (35 ml)/acetic acid (8 ml) mixture and refluxed overnight. The reaction mixture was allowed to cool to room temperature. Water was added and the mixture was cooled to 0° C. Sodium bicarbonate was added (ph=8) and then it was extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered, and concentrated to give 3-[5-(1-Amino-1-methyl-ethyl)-pyridin-2-ylamino]-5-bromo-1-methyl-1H-pyridin-2-one (2.2 g, 91%) as a yellow solid. MS (H+)=339.0.

Workup

  1. temperaturerefluxed overnight
  2. temperaturethe mixture was cooled to 0° C
  3. extractionit was extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7a172bbf776240c0a7494bc74af12a31
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

Loading…