Acetic Acid → N-{1-[6-(5-Bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino)-pyridin-3-yl]-1-methyl-ethyl}-2-chloro-acetamide

HRID 2069863Notes

Reaction equation

HRID 2069863 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](O)([CH3:19])[CH3:18])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.C(O)(=[O:23])C.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[Cl:35][CH2:36][C:37]#[N:38]>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:12]=[CH:13][C:14]([C:17]([NH:38][C:37](=[O:23])[CH2:36][Cl:35])([CH3:19])[CH3:18])=[CH:15][CH:16]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 7856ChloroacetonitrileHCID 516892Sodium BicarbonateHCID 594737935-Bromo-3-[5-(1-hydroxy-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-1H-pyridin-2-one

Product 1

HCID 59473779N-{1-[6-(5-Bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino)-pyridin-3-yl]-1-methyl-ethyl}-2-chloro-acetamideYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

5-Bromo-3-[5-(1-hydroxy-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-1H-pyridin-2-one (4.7 g, 13.9 mmol) was suspended in chloro acetonitrile (28 ml). Acetic acid (2.4 ml) was added to the suspension at ambient temperature and cooled to 0° C. Sulfuric acid, concentrated solution (2.4 ml) was added slowly to the cooled suspension. The reaction mixture was stirred 4 hr at room temperature then poured into ice. Ethyl acetate was added. Sodium bicarbonate was slowly added to neutralize the acidic mixture. A white precipitate was collected to give N-{1-[6-(5-Bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino)-pyridin-3-yl]-1-methyl-ethyl}-2-chloro-acetamide (4 g, 70%) as a off-white solid. MS (H+)=415.0

Workup

  1. additionthen poured into ice
  2. customA white precipitate was collected

Sources & evidence

ORD record
ord-c48099b06008404a875fd5a98c9c753d
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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