1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Amino-1-cyclopropyl-6,8-difluoro-7-[3-(1,2,4-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1742954

Reaktionsgleichung

[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.Cl.[N:23]1([CH:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)[CH:27]=[N:26][CH:25]=[N:24]1.C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:30]2[CH2:31][CH2:32][CH:28]([N:23]3[CH:27]=[N:26][CH:25]=[N:24]3)[CH2:29]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:16][CH2:17]1

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

To a suspension of 60 mg (0.2 mmol) of 5-amino -1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline -3-carboxylic acid and 80 mg of 3-(1,2,4-triazol-1-yl)pyrrolidine hydrochloride in 3 ml of dry pyridine under nitrogen was added 140 mg (0.9 mmol) of DBU, and the suspension was heated at 95° C. for 22 h. The resulting orange solution was then evaporated to dryness, water was added to the residue, and the orange solid was collected and washed with methanol to give 50 mg (60%) of yellowish solid after drying in vac-oven, m.p. 240.3°-242-3° C. 1H NMR (TFA) δ: 9.8 (s, 1H), 9.14 (s, 1H), 8.77 (s, 1H), 5.78-5.55 (m, 1H), 4.76-4.12 (m, 5H), 2.9-2.65 (m, 2H), 1.65-1.2 (m, 4H). Anal. calcd. for C19H18F 2 N6O3 : C, 54.81; H, 4.36; N, 20.17. Found: C, 54.52; H, 4.44; N, 20.00.

Aufarbeitung

customThe resulting orange solution was then evaporated to dryness, water
additionwas added to the residue
customthe orange solid was collected
washwashed with methanol

Quellen und Nachweise

ORD-Eintrag: ord-d40fec340b0549a58b9c49e79a548f1e
Quelldatensatz: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05342846

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