5-Amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → 5-Amino-1-cyclopropyl-6-fluoro-8-methoxy-7-[3-(4-methyl-1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1742986

Reaktionsgleichung

Cl.[CH3:2][C:3]1[N:4]=[N:5][N:6]([CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:7]=1.[NH2:13][C:14]1[C:23]([F:24])=[C:22](F)[C:21]([O:26][CH3:27])=[C:20]2[C:15]=1[C:16](=[O:34])[C:17]([C:31]([OH:33])=[O:32])=[CH:18][N:19]2[CH:28]1[CH2:30][CH2:29]1>N1C=CC=CC=1>[NH2:13][C:14]1[C:23]([F:24])=[C:22]([N:10]2[CH2:11][CH2:12][CH:8]([N:6]3[CH:7]=[C:3]([CH3:2])[N:4]=[N:5]3)[CH2:9]2)[C:21]([O:26][CH3:27])=[C:20]2[C:15]=1[C:16](=[O:34])[C:17]([C:31]([OH:33])=[O:32])=[CH:18][N:19]2[CH:28]1[CH2:30][CH2:29]1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

3-(4-methyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride (159 mg, 0.85 mmol) were added to a suspension of 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (100 mg, 0.34 mmol) in pyridine (5 ml). The reaction mixture was heated at 120° C. for 30 hrs, concentrated and the residue was triturated with water. The separated solid was filtered, washed with water and recrystallized from chloroform-hexane. Yield 52 mg; m.p. 255.6°-256.2 ° C. 1H NMR (TFA) δ: 9.39 (s, 1H), 8.40 (s, 1H), 5.77 (s, 1H), 4.34-4.83 (m, 4H), 4.10 (m, 1H), 3.79 (s, 3H), 2.89 (m, 2H), 2.68 (s, 3H), 1.22-1.67 (m, 4H).

Aufarbeitung

concentrationconcentrated
customthe residue was triturated with water
filtrationThe separated solid was filtered
washwashed with water
customrecrystallized from chloroform-hexane

Quellen und Nachweise

ORD-Eintrag: ord-90ae3760d3204fe6920963c67cb45a7d
Quelldatensatz: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05342846

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