Hydrochloric Acid → 2-(4-chloro-3-(4-fluorophenyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)ethanol
Reaktionsgleichung
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[N:10]([CH2:11][CH2:12]O)[N:9]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:7]=1[C:21]#[C:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH2:29].C(Cl)Cl.[ClH:33]>>[Cl:33][C:21]1[C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:1][N:5]=[C:6]2[N:10]([CH2:11][CH2:12][OH:29])[N:9]=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:7]=12Komponenten
6
Reaktionsbedingungen
- Temperatur
- -10 °C
Versuchsvorschrift
To a cooled (cooling bath −10° C.) stirred suspension of sodium nitrite (120 mg, 1.7 mmol) in conc. HCl (3.6 mL) was added 2-(5-amino-3-(4-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)ethanol (183 mg, 0.57 mmol) and the reaction mixture was allowed to warm to ambient temperature over 90 min. Water and CH2Cl2 were added to the reaction mixture. The aqueous phase was extracted with CH2Cl2 (×4) and the organic phases combined, dried over MgSO4, filtered and evaporated the crude material was purified using chromatography (silica gel, gradient 20 to 100% ethyl acetate/isohexane) followed by preparative HPLC yielding Compound 77 as a white solid (6.5 mg).
Aufarbeitung
- temperatureTo a cooled
- temperatureto warm to ambient temperature over 90 min
- extractionThe aqueous phase was extracted with CH2Cl2 (×4)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated the crude material
- customwas purified
Quellen und Nachweise
- ORD-Eintrag
- ord-1714bd83bef247aab2911a0cc1baedbf
- Quelldatensatz
- uspto-grants-2016_02
- Patentnummer
- US09260381B2
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