Hydrochloric Acid → 3-(5-Phenyl-1,2,4-oxadiazol-3-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine

HRID 1959417Notes

Reaction equation

HRID 1959417 reaction equation
Cl.O1CCOCC1.[NH2:8][C:9]1[N:10]=[CH:11][C:12]([C:26]2[CH2:27][CH2:28][N:29](C(OC(C)(C)C)=O)[CH2:30][CH:31]=2)=[N:13][C:14]=1[C:15]1[N:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:17][N:16]=1>CO>[C:20]1([C:18]2[O:17][N:16]=[C:15]([C:14]3[C:9]([NH2:8])=[N:10][CH:11]=[C:12]([C:26]4[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=4)[N:13]=3)[N:19]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66744707HCID 66744707, compound

Product 1

HCID 667444423-(5-Phenyl-1,2,4-oxadiazol-3-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amineYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of HCl in dioxane (505.5 μL of 4 M, 2.022 mmol) was added to a solution of tert-butyl 4-[5-amino-6-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylate (170 mg, 0.4043 mmol) in methanol (5 mL) at rt and the reaction mixture stirred at room temperature for 48 h. The reaction mixture was concentrated in vacuo to give the title compound (129 mg, 99% yield); MS (ES+) 321.03

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-9051fa0a4f6040c3940a19e1aedc3d14
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

Loading…