Hydrochloric Acid → HCID 178477980, compound

HRID 1851240Notes

Reaction equation

HRID 1851240 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[NH:14][N:13]=2)[CH2:9]1)=O)(C)(C)C.[ClH:23]>O1CCOCC1.C(OCC)C.CO>[ClH:23].[NH:8]1[CH2:11][CH:10]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[NH:14][N:13]=2)[CH2:9]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 178451665HCID 178451665, compound

Product 1

HCID 178477980HCID 178477980, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

3-(5-pyridin-2-yl-1H-[1,2,4]triazol-3-yl)-azetidine-1-carboxylic acid tert-butyl ester (3.13 g, 10.39 mmol) was suspended in a solution of HCl in dioxane (4M, 80 mL) and stirred at rt overnight. The reaction mixture was diluted with diethyl ether, filtered and the residue suspended in acetonitrile and stirred for 45 min at rt. The solid (hydroscopic) was isolated by filtration, partially dissolved in warm methanol and addition of diethyl ether resulted in precipitation of a yellow sticky solid which could not be filtered. The mixture was concentrated in vacuo and dried in a vacuum oven (40° C.) to obtain the desired compound as a light-yellow solid.

Workup

  1. filtrationfiltered
  2. stirringstirred for 45 min at rt
  3. customThe solid (hydroscopic) was isolated by filtration
  4. customresulted in precipitation of a yellow sticky solid which could not
  5. filtrationbe filtered
  6. concentrationThe mixture was concentrated in vacuo
  7. customdried in a vacuum oven (40° C.)

Sources & evidence

ORD record
ord-8e3993b804074c918349a2252c5f23a9
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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