Hydrochloric Acid → 3-[3-Methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acid

HRID 1398178Notes

Reaction equation

HRID 1398178 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:19]3[CH2:20][CH2:21][CH2:22][C:23]([CH3:29])([C:24]([O:26]CC)=[O:25])[C:18]3=[N:17][N:16]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][C:12]([CH3:14])=[N:11][CH:10]=1.[OH-].[Na+].Cl>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:19]3[CH2:20][CH2:21][CH2:22][C:23]([CH3:29])([C:24]([OH:26])=[O:25])[C:18]3=[N:17][N:16]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][C:12]([CH3:14])=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66608009Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

Product 1

HCID 666082883-[3-Methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acidYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (1.5 g), 1N aqueous sodium hydroxide solution (7.57 mL) and THF (8 mL) was stirred at room temperature for 16 hr. The reaction mixture was acidified with 1N hydrochloric acid, and the organic layer was evaporated under reduced pressure. The mixture was stirred at room temperature for 30 min, and the obtained solid was collected by filtration to give the title compound (1.36 g).

Workup

  1. customthe organic layer was evaporated under reduced pressure
  2. stirringThe mixture was stirred at room temperature for 30 min
  3. filtrationthe obtained solid was collected by filtration

Sources & evidence

ORD record
ord-93512107965b42ccb10bd07a8477e831
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

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