Sodium Hydroxide → HCID 68515198, compound

HRID 1717240Notes

Reaction equation

HRID 1717240 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([N:11]2[C:15]([CH2:16][CH2:17][CH3:18])=[C:14]([C:19]([O:21]C)=[O:20])[N:13]=[N:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([N:11]2[C:15]([CH2:16][CH2:17][CH3:18])=[C:14]([C:19]([OH:21])=[O:20])[N:13]=[N:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68516506HCID 68516506, compound

Product 1

HCID 68515198HCID 68515198, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 1-[6-(acetylamino)pyridin-3-yl]-5-propyl-1H-1,2,3-triazole-4-carboxylate (0.55 g) obtained in Example 26d) in ethanol (5 ml) was added 8N aqueous sodium hydroxide solution (0.45 ml), and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, toluene (5 ml) was added to the residue. The solvent was evaporated under reduced pressure. To a solution of the residue in acetonitrile (10 ml) was added 4N hydrochloric acid-ethyl acetate solution (0.9 ml) to give a solution of 1-[6-(acetylamino)pyridin-3-yl]-5-propyl-1H-1,2,3-triazole-4-carboxylic acid in acetonitrile. Then, cyclopropylamine (0.15 ml), triethylamine (0.31 ml), HOBt (0.34 g) and WSC (0.42 g) were successively added, and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, the residue was dissolved in ethyl acetate and washed with aqueous sodium hydrogen carbonate solution. 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) to give the title compound as a pale-green powder (0.22 g, 41%).

Workup

  1. customThe solvent was evaporated under reduced pressure, toluene (5 ml)
  2. additionwas added to the residue
  3. customThe solvent was evaporated under reduced pressure
  4. additionTo a solution of the residue in acetonitrile (10 ml) was added 4N hydrochloric acid-ethyl acetate solution (0.9 ml)

Sources & evidence

ORD record
ord-e374606a44fd417aa8febcdb265ab075
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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