Reaktionsgleichung
C[O:2][C:3]([C:5]1[N:6]=[N:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[CH2:13][CH2:12]2)=[CH:9][CH:10]=1)=[O:4].O[Li].O>O1CCCC1.O>[F:27][C:24]([F:25])([F:26])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:17]([N:14]1[CH2:15][CH2:16][N:11]([C:8]2[N:7]=[N:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=2)[CH2:12][CH2:13]1)=[O:28]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a suspension of 6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid methyl ester (1.000 g, 2.535 mmol) in a mixture of tetrahydrofuran-water (1:1, 5 mL), LiOH.H2O (0.106 g, 2.535 mmol) was added in one portion. The mixture was stirred at room temperature overnight. The clear solution was then cooled to 0° C. and quenched with 1 N HCl solution to pH 4-5. The solid separated was filtered. The residue was washed with cold water and dried under vacuum to obtain 6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (0.771 g, 2.027 mmol, 80%) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 7.82 (t, J=9.6 Hz, 2H), 7.74 (t, J=7.4 Hz, 1H), 7.64 (t, J=7.6 Hz, 1H), 7.52 (d, J=7.4 Hz, 1H), 7.27 (t, J=9.6 Hz, 1H), 3.87-3.60 (m, 6H), 3.31-3.10 (m, 2H), 13C NMR (75 MHz, DMSO-d6) δ 166.8, 165.7, 160.0, 143.7, 134.9, 134.9, 133.4, 130.1, 129.0, 128.0, 127.1, 127.0, 127.0, 126.0, 125.9, 125.5, 122.4, 112.5, 46.3, 44.3, 44.1. MS (ES+) m/z 381.2 (M+1).
Aufarbeitung
- additionwas added in one portion
- temperatureThe clear solution was then cooled to 0° C.
- customquenched with 1 N HCl solution to pH 4-5
- customThe solid separated
- filtrationwas filtered
- washThe residue was washed with cold water
- customdried under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-cd891da7ad1c4888befa457d5e1376a8
- Quelldatensatz
- uspto-grants-2010_08
- Patentnummer
- US07767677B2
Verknüpfte Notizen
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