Hydrochloric Acid → HCID 178488932, compound

HRID 1851253Notes

Reaction equation

HRID 1851253 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:18]=[C:17]([C:19]3[CH:20]=[N:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)[NH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C1COCC1.O1CCOCC1>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[NH:16][N:15]=[C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:18]=2)=[CH:20][N:21]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178488933HCID 178488933, compound

Product 1

HCID 178488932HCID 178488932, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-[5-(6-methoxy-pyridin-3-yl)-1H-[1,2,4]triazol-3-yl]-piperidine-1-carboxylic acid tert-butyl ester (1.23 g, prepared in analogy to intermediate example 44) in THF (15 mL) was treated with 4M HCl in dioxane (1.19 mL) and the reaction stirred at 50° C. for 1 hour. On cooling, the reaction was stirred overnight at rt. The volatiles were removed in vacuo and the residue was dissolved in water, made basic with 2M aqueous NaOH solution and extracted with EtOAc. The aqueous phase was extracted with CH2Cl2/MeOH, the organic phase was washed with brine and concentrated in vacuo to give the crude title compound which was used without further purification.

Workup

  1. temperatureOn cooling
  2. stirringthe reaction was stirred overnight at rt
  3. customThe volatiles were removed in vacuo
  4. dissolutionthe residue was dissolved in water
  5. extractionextracted with EtOAc
  6. extractionThe aqueous phase was extracted with CH2Cl2/MeOH
  7. washthe organic phase was washed with brine
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f6424f369c34512b06bb8fe881182a8
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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