1-Chloro-3-(2-trifluoromethyl-phenyl)-isoquinoline → HCID 178506126, Verbindung

HRID 38197

Reaktionsgleichung

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])[N:3]=1.[NH:22]1[CH:26]=[N:25][C:24]([NH2:27])=[N:23]1>C(O)C>[NH:22]1[CH:26]=[N:25][C:24]([NH:27][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:18]([F:21])([F:20])[F:19])[N:3]=2)=[N:23]1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A solution of 1-chloro-3-(2-trifluoromethyl-phenyl)-isoquinoline (0.326 mmol) and 1H-[1,2,4]triazol-3-ylamine (0.651 mmol) in ethanol (3 mL) was heated at 160° C. and the solvent evaporated with a stream of nitrogen. The remaining oil was then heated at 160° C. for 18 hours under nitrogen. The resulting melt was dissolved in 5% methanol/dichloromethane (50 mL), washed with saturated aqueous sodium bicarbonate (1×25 mL) then dried over magnesium sulfate. Purification by silica gel chromatography afforded IX-175 as a colorless oil (4% yield). 1H NMR (500 MHz, CDCl3) δ 9.18 (d, 1H), 8.82 (s, 1H), 7.90 (d, 1H), 7.85-7.75 (m, 3H), 7.71-7.62 (m, 3H), 7.60-7.55 (m, 2H), 4.42-4.35 (m, 1H). LC-MS (ES+) 356.16 (M+H); HPLC-Method D, Rt 3.55 min.

Aufarbeitung

customthe solvent evaporated with a stream of nitrogen
dissolutionThe resulting melt was dissolved in 5% methanol/dichloromethane (50 mL)
washwashed with saturated aqueous sodium bicarbonate (1×25 mL)
dry with materialthen dried over magnesium sulfate
customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-c5af4557678c4de9881b97505b1a30f1
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08524720B2

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