Pyridine → 1-(2-Chloro-6H,12H-5-oxa-11-aza-dibenzo[a,e]cycloocten-11-yl)-ethanone

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Reaktionsgleichung

[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[NH:10][CH2:11][C:4]=2[CH:3]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[N:10]([C:18](=[O:20])[CH3:19])[CH2:11][C:4]=2[CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a stirred solution of 2-Chloro-11,12-dihydro-6H-5-oxa-11-aza-dibenzo[a,e]cyclooctene Example 348C (43 mg, 0.18 mmol) and DMAP (4.27 mg, 34.9 μmol) in toluene (1.25 mL) was added acetic anhydride (36.0 μL, 0.39 mmol) and pyridine (13.9 mg, 0.18 mmol). This reaction mixture was heated at 80° C. for 50 min, cooled to room temperature and concentrated in vacuo. This was purified by a Shimadzu auto prep HPLC, employing 20% to 100% 10 min gradient elution with 0.1% TFA in MeOH-water solvent system, 220 nM detection, 20 mL/min elution with a YMC ODS S5 20×100 mm column to give 27.7 mg of desired 1-(2-Chloro-6H,12H-5-oxa-11-aza-dibenzo[a,e]cycloocten-11-yl)-ethanone Example 348D in 55% yield. HPLC Rt=3.09 min (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm) LC/MS: M+H=288

Aufarbeitung

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customThis was purified by a Shimadzu auto prep HPLC
wash20% to 100% 10 min gradient elution
washwith 0.1% TFA in MeOH-water solvent system, 220 nM detection, 20 mL/min elution with a YMC ODS

Quellen und Nachweise

ORD-Eintrag: ord-ca19b40d0e18460f8cd7c38a61e1e8a9
Quelldatensatz: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07417040B2

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