Methanol → HCID 90013599, Verbindung

HRID 1051235

Reaktionsgleichung

[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][C@H:24]4[CH2:28][CH2:27][O:26][CH2:25]4)=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].Cl.N.CO.O>[Fe].CC(=O)OCC>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][C@H:24]4[CH2:28][CH2:27][O:26][CH2:25]4)=[C:17]([NH2:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

(S)—N-(3-ethynylphenyl)-6-nitro-7-(tetrahydrofuran-3-yloxy)quinazolin-4-amine (4 g, 0.011 mol) and ammonia hydrochloride (2.4 g, 0.045 mol) was mixed in a solution of 150 mL methanol, 75 mL H2O, 50 ml EA, and then was heated to 70° C. Fe (4.8 g, 0.085 mol) was added and the reaction mixture was heated to reflux for 4 hours. The resulting reaction solution was filtered and concentrated under reduced pressure to remove most of solvent. The residue was diluted in 100 mL H2O, extracted with ethyl acetate (3×100 mL), the organic layers were concentrated to give (S)—N4-(3-ethynylphenyl)-7-(tetrahydrofuran-3-yloxy)quinazoline-4,6-diamine as grey solid 1.8 g (48.9% yield).

Aufarbeitung

temperaturethe reaction mixture was heated
temperatureto reflux for 4 hours
customThe resulting reaction solution
filtrationwas filtered
concentrationconcentrated under reduced pressure
customto remove most of solvent
additionThe residue was diluted in 100 mL H2O
extractionextracted with ethyl acetate (3×100 mL)
concentrationthe organic layers were concentrated

Quellen und Nachweise

ORD-Eintrag: ord-78ad331bab724c7e9e1947e7fda91800
Quelldatensatz: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09388170B2

Verknüpfte Notizen

Wird geladen…