Piperidine → HCID 178454331, compound

HRID 719855Notes

Reaction equation

[CH3:1][C:2]([CH3:23])([O:4][C:5]([N:7]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]1[N:9]=[CH:10][C:11]([C:14]#[N:15])=[N:12][CH:13]=1)=[O:6])[CH3:3].Cl.[NH2:25][OH:26].N1CCCCC1>CS(C)=O>[CH3:21][C:19]([CH3:22])([O:18][C:16]([N:7]([C:5]([O:4][C:2]([CH3:23])([CH3:3])[CH3:1])=[O:6])[C:8]1[N:9]=[CH:10][C:11]([C:14](=[NH:15])[NH:25][OH:26])=[N:12][CH:13]=1)=[O:17])[CH3:20]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 5-[[bis[(1,1-dimethylethoxy)carbonyl]]amino]-2-pyrazinecarbonitrile (305.7 mg, 0.954 mmol) in dimethyl sulfoxide (5.8 mL) was treated with hydroxylamine hydrochloride (333.8 mg, 4.804 mmol) and piperidine (0.50 mL, 5.050 mmol). The reaction was stirred at 25° C. for 50 min and then was partitioned between ethyl acetate (100 mL) and water (50 mL). The organic layer was washed with water (50 mL) and a saturated aqueous sodium chloride solution (50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40L, Silica, 1/3 ethyl acetate/hexanes) afforded the 5-[[bis[(1,1-dimethylethoxy)carbonyl]]amino]-N-hydroxy-2-pyrazinecarboximidamide as a white solid (186.2 mg, 55%): mp 185–186° C.; (ES)+-HRMS m/e calcd for C15H23N5O5 (M+H)+ 354.1772, found 354.1775.

Workup

customwas partitioned between ethyl acetate (100 mL) and water (50 mL)
washThe organic layer was washed with water (50 mL)
dry with materiala saturated aqueous sodium chloride solution (50 mL), dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2e6a08133e2d4af892f162be9027c3d6
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132425B2

Reaction notes

Loading…