Hydrochloric Acid → HCID 56961402, Verbindung

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Reaktionsgleichung

[O:1]1[CH:5]=[CH:4][C:3]([C:6](=O)[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:2]1.[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]=1[OH:26])[CH:21]=O)[CH3:16].[NH2:30][C:31]([NH2:33])=[O:32].Cl>CCO>[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([CH:21]2[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:6]([C:3]3[CH:4]=[CH:5][O:1][CH:2]=3)[NH:33][C:31](=[O:32])[NH:30]2)[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]=1[OH:26])[CH3:16]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of 1-(furan-3-yl)-2-phenylethanone (Intermediate 22) (692 mg, 3.72 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (942 mg, 4.46 mmol), and urea (669.6 mg, 11.16 mmol) in anhydrous EtOH (5 mL) was added concentrated HCl solution (0.2 mL), and the reaction mixture was refluxed (110° C.) for thirteen hours. TLC (eluting with EtOAc) showed that the most of the starting materials were consumed. The reaction mixture was concentrated, and purified by column chromatography and preparative HPLC to afford Compound 50 as a yellow solid (173 mg, yield: 11.0%). 1H NMR (DMSO-d6 400 MHz TMS): δ10.26 (s, 1H), 8.478 (s, 1H), 6.981-7.708 (m, 10H), 5.766 (s, 1H), 5.141 (d, J=2.4 Hz, 1H), 3.918-4.061 (m, 2H), 1.304 (t, J=6.8 Hz, 3H); MS (ESI): m/z 422.1[M+1]+.

Aufarbeitung

washTLC (eluting with EtOAc)
customwere consumed
concentrationThe reaction mixture was concentrated
custompurified by column chromatography and preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-dbf291ca42c14ae792fe1d7757dbac8b
Quelldatensatz: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09283229B2

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