Hydrochloric Acid → 5-[2-(4-Aminopiperidin-1-yl)-6-chloropyridin-4-yl]-1,3,4-oxadiazol-2(5H)-one hydrochloride

HRID 2233846Notes

Reaction equation

HRID 2233846 reaction equation
Cl.[Cl:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([NH:15]C(=O)OC(C)(C)C)[CH2:11][CH2:10]2)[CH:6]=[C:5]([CH:23]2[N:27]=[N:26][C:25](=[O:28])[O:24]2)[CH:4]=1>O1CCOCC1>[ClH:2].[NH2:15][CH:12]1[CH2:13][CH2:14][N:9]([C:7]2[CH:6]=[C:5]([CH:23]3[O:24][C:25](=[O:28])[N:26]=[N:27]3)[CH:4]=[C:3]([Cl:2])[N:8]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86608245tert-Butyl 1-[6-chloro-4-(5-oxo-2,5-dihydro-1,3,4-oxadiazol-2-yl)pyridin-2-yl]piperidin-4-ylcarbamate2×

Product 1

HCID 866082465-[2-(4-Aminopiperidin-1-yl)-6-chloropyridin-4-yl]-1,3,4-oxadiazol-2(5H)-one hydrochlorideYield 188.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4 N Hydrochloric acid in dioxane (3 ml) was added to tert-butyl 1-[6-chloro-4-(5-oxo-2,5-dihydro-1,3,4-oxadiazol-2-yl)pyridin-2-yl]piperidin-4-ylcarbamate (Intermediate 50, 0.12 mg, 0.32 mmol). The mixture was stirred at room temperature for 45 min, then concentrated in vacuo to afford the title compound (100 mg).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a9db109a7eb45e9a738bff809330a68
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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