Hydrazine hydrate (1:1) → N',5-diamino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazine-2-carboximidamide

HRID 1749053Notes

Reaction equation

O.[NH2:2][NH2:3].[NH2:4][C:5]1[N:6]=[CH:7][C:8]([C:20]#[N:21])=[N:9][C:10]=1[C:11]1[O:12][C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])=[N:14][N:15]=1>CC(O)C>[NH2:4][C:5]1[N:6]=[CH:7][C:8](/[C:20](=[N:2]/[NH2:3])/[NH2:21])=[N:9][C:10]=1[C:11]1[O:12][C:13]([C:16]([CH3:18])([CH3:17])[CH3:19])=[N:14][N:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Hydrazine hydrate (82 mL, 1.69 mol) was added to 5-amino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazine-2-carbonitrile (55 g, 225.18 mmol) in IPA (200 mL) and the mixture was heated at 50° C. under nitrogen for 16 hours. The mixture was cooled in an ice bath. The resulting precipitate was collected by filtration, washed with IPA and diethyl ether and dried to a constant weight to afford (Z)-5-amino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazine-2-carbohydrazonamide (49.2 g, 79%) as a yellow solid: 1H NMR Spectrum: (DMSO-d6) 1.45 (9H, s), 5.26 (2H, s), 5.58 (2H, s), 7.56 (2H, s), 8.75 (1H, s); Mass Spectrum [M+H]+=277.

Workup

temperatureThe mixture was cooled in an ice bath
filtrationThe resulting precipitate was collected by filtration
washwashed with IPA and diethyl ether
customdried to a constant weight

Sources & evidence

ORD record: ord-d5b03b9273b746d8ad0f51f7b953d07b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09155727B2

Reaction notes

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