Hydrochloric Acid → 3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid

HRID 62475Notes

Reaction equation

HRID 62475 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[N:7]2[CH2:8][CH2:9][CH:10]([C:12]([O:14]CC)=[O:13])[CH2:11][C:6]2=[N:5][N:4]=1.O[Li].O.Cl>C1COCC1.O>[F:18][C:2]([F:1])([F:17])[C:3]1[N:7]2[CH2:8][CH2:9][CH:10]([C:12]([OH:14])=[O:13])[CH2:11][C:6]2=[N:5][N:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 90304476Ethyl 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine-7-carboxylate

Product 1

HCID 838664073-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine-7-carboxylate (2.28 g, 8.662 mmol) in THF (17 mL) was added 4N LiOH.H2O (726.9 mg, 17.324 mmol) in water (4 mL), then the mixture was stirred at room temperature for 2 h, then acidified with 1N HCl to pH=3. The resulting mixture was extracted with EA and the aqueous phase was directly drying to give 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid without further purification.

Workup

  1. extractionThe resulting mixture was extracted with EA
  2. customthe aqueous phase was directly drying

Sources & evidence

ORD record
ord-d0b21d08d35f4db4a6e350343310bd0e
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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