Pyridine → HCID 68517286, compound

HRID 1717233Notes

Reaction equation

HRID 1717233 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][CH2:14][CH3:15])=[C:11]([C:16]([NH:18][CH:19]3[CH2:21][CH2:20]3)=[O:17])[N:10]=[N:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:28][CH:29]([CH3:33])[C:30](Cl)=[O:31]>ClCCl>[CH:19]1([NH:18][C:16]([C:11]2[N:10]=[N:9][N:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:30](=[O:31])[CH:29]([CH3:33])[CH3:28])=[CH:3][CH:4]=3)[C:12]=2[CH2:13][CH2:14][CH3:15])=[O:17])[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 685175481-(4-aminophenyl)-N-cyclopropyl-5-propyl-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 68517286HCID 68517286, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(4-aminophenyl)-N-cyclopropyl-5-propyl-1H-1,2,3-triazole-4-carboxamide (0.29 g) obtained in Example 1d) and pyridine (0.09 ml) in dichloromethane (3 ml) was added 2-methylpropanoyl chloride (0.1 ml) under ice-cooling, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, and washed successively with diluted hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate), and the obtained product was washed with diisopropyl ether to give the title compound as a pale-yellow powder (0.21 g, 60%).

Workup

  1. temperaturecooling
  2. washwashed successively with diluted hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)
  6. washthe obtained product was washed with diisopropyl ether

Sources & evidence

ORD record
ord-5fd3c8a473d9440a99275b50e340b369
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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