O-tert-butylhydroxylamine hydrochloride → N-[5-(1-tert-butoxyimino-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide

HRID 719891Notes

Reaction equation

[C:1]([C:4]1[N:5]=[CH:6][C:7]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:8][CH:9]=1)(=O)[CH3:2].Cl.[C:18]([O:22][NH2:23])([CH3:21])([CH3:20])[CH3:19]>CO.N1C=CC=CC=1>[C:18]([O:22][N:23]=[C:1]([C:4]1[N:5]=[CH:6][C:7]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:8][CH:9]=1)[CH3:2])([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of N-(5-acetyl-pyrazin-2-yl)-2,2-dimethyl-propionamide (800.0 mg, 3.62 mmol) in methanol (9 mL) and pyridine (9 mL) was treated with O-(tert-butyl)hydroxylamine hydrochloride (681.1 mg, 5.42 mmol). The resulting reaction mixture was heated under reflux for 30 min. The reaction mixture was allowed to cool to 25° C. and then was concentrated in vacuo. The resulting residue was diluted with ethyl acetate (50 mL). The organic layer was washed with a 1N aqueous hydrochloric acid solution (1×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 1/9 ethyl acetate/hexanes) afforded N-[5-(1-tert-butoxyimino-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide (1.04 g, 98%) as a white solid: mp 123–124° C.; EI-HRMS m/e calcd for C15H24N4O2 (M+) 292.1899, found 292.1901.

Workup

customThe resulting reaction mixture
temperaturewas heated
temperatureunder reflux for 30 min
concentrationwas concentrated in vacuo
additionThe resulting residue was diluted with ethyl acetate (50 mL)
washThe organic layer was washed with a 1N aqueous hydrochloric acid solution (1×50 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6d561c83aa3046cf96d68aef89b367f8
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132425B2

Reaction notes

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