Ethyl Acetate → 3-[{2-(1-Tert-butoxycarbonylpiperidin-4-yl)ethyl}carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole

HRID 54563Notes

Reaction equation

C(O[C:4]([C:6]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[O:8][N:7]=1)=[O:5])C.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33][NH2:34])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(OCC)(=O)C>CN(C)C=O>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33][NH:34][C:4]([C:6]2[N:10]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=3)[O:8][N:7]=2)=[O:5])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 3-ethoxycarbonyl-5-(4-cyanophenyl)-1,2,4-oxadiazole (2.0 g) and 2-(1-tert-butoxycarbonylpiperidin-4-yl)ethylamine in N,N-dimethylformamide (1 ml) was heated at 120° C. for 5 hours. The mixture was dissolved with ethyl acetate, washed with water, brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethanol to afford 3-[{2-(1-tert-butoxycarbonylpiperidin-4-yl)ethyl}carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole (2.6 g).

Workup

washwashed with water, brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-1224fa790a994fbf9ceb4726555c59b7
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05622976

Reaction notes

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