3-Fluorobenzyl bromide → [1-(3-Fluoro-benzyl)-piperidin-4-yl]-methyl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine
Reaktionsgleichung
[CH3:1][N:2]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[C:3]1[S:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][N:7]=1.[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Br.C(N(C(C)C)CC)(C)C>C(#N)C.ClCCl>[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][N:15]1[CH2:16][CH2:17][CH:12]([N:2]([CH3:1])[C:3]2[S:4][C:5]([C:8]([F:11])([F:9])[F:10])=[N:6][N:7]=2)[CH2:13][CH2:14]1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A mixture of methyl-piperidin-4-yl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine (D2) (0.050 g, 0.19 mmol), 3-fluorobenzyl bromide (0.030 ml, 0.24 mmol) and diisopropylethylamine (0.050 ml, 0.28 mmol) in acetonitrile (3 ml) was stirred at 100° C. for 5 min., under microwave irradiation. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and extracted with a 10% solution of ammonium chloride (25 ml). The organic layer was separated, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 0-1.5% ammonia in methanol (7M)/dichloromethane) to yield E2 (0.062 g, 88%) as a solid. C16H18F4N4S requires 374. Found 375 (MH+).
Aufarbeitung
- temperatureAfter cooling to room temperature
- extractionextracted with a 10% solution of ammonium chloride (25 ml)
- customThe organic layer was separated
- dry with materialdried (Na2SO4)
- customthe solvent evaporated in vacuo
- customThe crude product was purified by flash column chromatography (silica gel; 0-1.5% ammonia in methanol (7M)/dichloromethane)
Quellen und Nachweise
- ORD-Eintrag
- ord-f864752e589e457a9b17917bceabb696
- Quelldatensatz
- uspto-grants-2015_01
- Patentnummer
- US08933101B2
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