Diisopropylethylamine → N-(3-isoxazolyl)-2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetamide

HRID 1009740

Reaktionsgleichung

Cl.CN(C)CCCN=C=NCC.OC1C=CC=C[N+]=1[O-].[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][C:32]=1[O:33][CH3:34])[N:29]=[CH:28][CH:27]=[C:26]2[O:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][C:43]([OH:45])=O)=[CH:38][CH:37]=1.[NH2:46][C:47]1[CH:51]=[CH:50][O:49][N:48]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[O:49]1[CH:50]=[CH:51][C:47]([NH:46][C:43](=[O:45])[CH2:42][C:39]2[CH:38]=[CH:37][C:36]([O:35][C:26]3[C:25]4[C:30](=[CH:31][C:32]([O:33][CH3:34])=[C:23]([O:22][CH3:21])[CH:24]=4)[N:29]=[CH:28][CH:27]=3)=[CH:41][CH:40]=2)=[N:48]1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.226 g) and 2-hydroxypyridine N-oxide (0.131 g) were added in turn to a stirred mixture of 2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetic acid (0.2 g), 3-aminoisoxazole (0.064 g), diisopropylethylamine (0.226 g) and DMF (3 ml) at ambient temperature. The resultant mixture was stirred and heated to 60° C. for 16 hours. The mixture was evaporated and the residue was purified by preparative HPLC using a Waters ‘Xterra’ reversed-phase column (5 microns silica, 30 mm diameter, 150 mm length) using decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetoliitrile as eluent. There was thus obtained the title compound (0.035 g); 1H NMR: (DMSOd6) 3.76 (s, 2H), 3.92 (s, 3H), 3.95 (s, 3H), 6.47 (d, 1H), 6.93 (d, 1H), 7.23 (d, 2H), 7.4 (s, 1H), 7.46 (d, 2H), 7.49 (s, 1H), 8.49 (d, 1H), 8.80 (d, 1H), 11.33 (br s, 1H); Mass Spectrum: M+H+ 406.

Aufarbeitung

customThe mixture was evaporated
customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-8f22dcf49de44c3b9102b72f31afc206
Quelldatensatz: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07973164B2

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