Acetic Acid → N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)propan-2-yl)acetamide

HRID 2069867Notes

Reaction equation

HRID 2069867 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:21]([OH:24])(=O)[CH3:22].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].C(#[N:37])C>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:37][C:21](=[O:24])[CH3:22])([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 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 594737935-Bromo-3-[5-(1-hydroxy-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-1H-pyridin-2-one

Product 1

HCID 59473804N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)propan-2-yl)acetamideYield 34%

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 (180 mg, 0.532 mmol) was dissolved in acetonitrile (10 ml). Acetic acid (0.5 ml) was added at room temperature, and then cooled to 0° C. Sulfuric acid, concentrated solution (0.5 ml) was added slowly to the cooled solution. The reaction mixture was allowed to warm up to room temperature after the addition and stirred overnight. The reaction mixture was poured into ice and ethyl acetate was added. Sodium bicarbonate was added slowly to neutralize the acidic mixture and the it was extracted with ethyl acetate, washed with brine and dried over sodium sulfate. The mixture was filtered and concentrated. Crude material was purified by 24 g column with 0-10% MeOH in EtOAc 1:1 Hex to give N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)propan-2-yl)acetamide (69 mg, 34%) as a yellow solid. MS (H+)=379.0.

Workup

  1. temperatureto warm up to room temperature
  2. additionafter the addition
  3. additionwas added
  4. extractionthe it was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated
  9. customCrude material was purified by 24 g column with 0-10% MeOH in EtOAc 1:1 Hex

Sources & evidence

ORD record
ord-5dd04e5c06604eda9cabc9371c327991
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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