1-(Thien-2-ylcarbonyl)piperazine → 6-Fluoro-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester

HRID 901259

Reaktionsgleichung

Reaktionsgleichung von HRID 901259
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:18])[NH:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][C:12]([F:17])=[CH:11][N:10]=2)=[O:5])[CH3:2].[N:19]1([C:25]([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)=[O:26])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:18])[NH:8][C:9]2[C:14]([C:15]=1[N:22]1[CH2:23][CH2:24][N:19]([C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[O:26])[CH2:20][CH2:21]1)=[CH:13][C:12]([F:17])=[CH:11][N:10]=2)=[O:5])[CH3:2]

Komponenten

3

Edukt 2

HCID 7975621-(Thien-2-ylcarbonyl)piperazineHCID 692189084-Chloro-6-fluoro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester

Produkt 1

HCID 692171586-Fluoro-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester

Versuchsvorschrift

This compound was prepared from 4-chloro-6-fluoro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (78) and piperazine-1-yl-thiophene-2-yl-methanone according to general procedure E. Yield 3.16 g (66%), MP 124-133° C.; 1H-NMR (DMSO-d6): δ 1.26 (t, J=7.2 Hz, 3H), 3.11 (m, 4H), 3.88 (m, 4H), 4.28 (q, J=7.2 Hz, 2H), 7.15 (dd, J=3.6, 4.8 Hz, 1H), 7.45 (dd, J=1.2, 3.6 Hz, 1H), 7.79 (dd, J=1.2, 4.8 Hz, 1H), 8.05 (dd, J=2.8, 8.0 Hz, 1H), 8.63 (d, J=2.8 Hz, 1H) 12.40 (s, 1H); EIMS: 431 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-37a1f490d8a14f33af380c524b9f85dd
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361760B2

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