Hydroxylamine → Tert-butyl ({5-[amino(hydroxyimino)methyl]-3-chloropyridin-2-yl}amino)acetate

HRID 1631012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1631012
[NH2:1][OH:2].[Cl:3][C:4]1[C:5]([NH:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[N:6][CH:7]=[C:8]([C:10]#[N:11])[CH:9]=1>C1COCC1>[NH2:11][C:10](=[N:1][OH:2])[C:8]1[CH:9]=[C:4]([Cl:3])[C:5]([NH:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 787HydroxylamineHCID 58554110Tert-butyl [(3-chloro-5-cyanopyridin-2-yl)amino]acetate

Produkt 1

HCID 76828193Tert-butyl ({5-[amino(hydroxyimino)methyl]-3-chloropyridin-2-yl}amino)acetateAusbeute 101 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Hydroxylamine (1.5 mL, 39.5 mmol) was added into a solution of tert-butyl [(3-chloro-5-cyanopyridin-2-yl)amino]acetate (2.1 g, 7.9 mmol) in THF (30 mL) under nitrogen. The reaction mixture was stirred at RT for 48 hours, and then was concentrated under reduced pressure to afford the title compound as a white solid (2.4 g, quantitative). LC/MS, M+(ESI): 301.0. 1H NMR (DMSO-d6, 400 MHz) δ 9.52 (1H, s), 8.24 (1H, d), 7.81 (1H, d), 7.04 (1H, t), 5.80 (2H, s), 3.95 (2H, m), 1.37 (9H, s).

Aufarbeitung

  1. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-52df734da1cd4fc7a22108b0804007e3
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791142B2

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