Acetic Anhydride → 4-(5-Acetoxy-4-chloro-2-fluoroanilino)-7-benzyloxy-6-methoxycinnoline

HRID 7473

Reaktionsgleichung

[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([O:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:26][C:27]3C=C(O)[C:30]([Cl:34])=[CH:29][C:28]=3[F:35])=[CH:21][N:22]=[N:23]2)=[CH:18][C:17]=1[O:36][CH3:37])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:5]([O:4][C:1]1[C:30]([Cl:34])=[CH:29][C:28]([F:35])=[C:27]([CH:2]=1)[NH:26][C:20]1[C:19]2[C:24](=[CH:25][C:16]([O:15][CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[C:17]([O:36][CH3:37])[CH:18]=2)[N:23]=[N:22][CH:21]=1)(=[O:7])[CH3:6]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

Acetic anhydride (920 μl, 9.7 mmol) and 4-dimethylaminopyridine (80 mg, 0.65 mmol) were added to a suspension of 7-benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxycinnoline (3 g, 6.5 mmol), (prepared as described in Example 6), in pyridine (50 ml). After heating at 110° C. for 25 minutes, the solid was filtered off, washed with water and ether and dried under vacuum. The solid was suspended in 2M ethereal hydrogen chloride and the volatiles removed by evaporation to give 4-(5-acetoxy-4-chloro-2-fluoroanilino)-7-benzyloxy-6-methoxycinnoline as the hydrochloride salt (yellow solid, 3.1 g, 94%).

Aufarbeitung

filtrationthe solid was filtered off
washwashed with water and ether
customdried under vacuum
customthe volatiles removed by evaporation

Quellen und Nachweise

ORD-Eintrag: ord-86f02a2df9b34f72ae5e90ef9abd5f91
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07087602B2

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