Ethyl Acetate → N-(3,5-Dimethylphenyl)-2-[2-(N'-n-propylureido)pyridin-4-ylmethylthio]pyridine-3-carboxamide

HRID 1984716Notes

Reaction equation

HRID 1984716 reaction equation
[CH2:1]([N:4]=[C:5]=[O:6])[CH2:2][CH3:3].[NH2:7][C:8]1[CH:13]=[C:12]([CH2:14][S:15][C:16]2[C:21]([C:22]([NH:24][C:25]3[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[CH:26]=3)=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:11]=[CH:10][N:9]=1.C(OCC)(=O)C>CN(C)C=O>[CH3:32][C:27]1[CH:26]=[C:25]([NH:24][C:22]([C:21]2[C:16]([S:15][CH2:14][C:12]3[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[O:6])[CH:13]=3)=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:23])[CH:30]=[C:29]([CH3:31])[CH:28]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 61033Propyl isocyanateHCID 111644062-(2-aminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

Product 1

HCID 11305473N-(3,5-Dimethylphenyl)-2-[2-(N'-n-propylureido)pyridin-4-ylmethylthio]pyridine-3-carboxamideYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

n-Propyl isocyanate (20 mg, 0.23 mmol) was added to a solution of 2-(2-aminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide (The free base of Compound No. 3-1, 28 mg, 0.077 mmol) in N,N-dimethylformamide (0.60 mL) at room temperature, and the mixture was stirred for 4 hours at 80° C. Ethyl acetate (10 mL) was added to the reaction mixture, the whole was washed with water (15 mL) and brine (15 mL), and then the organic layer was dried over anhydrous magnesium sulfate. The organic layer was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 12 mg of the target compound as a colorless solid(Yield 33%).

Workup

  1. washthe whole was washed with water (15 mL) and brine (15 mL)
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe organic layer was evaporated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-be4920ea477e49c4be662110cf7719a8
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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