Reaktionsgleichung
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:11])=[N:9][N:10]=2)[N:7]=1.[CH3:12][NH:13][C@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15]>CN1C(=O)CCC1>[CH3:12][N:13]([C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:11])=[N:9][N:10]=2)[N:7]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 200 °C
Versuchsvorschrift
6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine (120 mg, 0.712 mmol; commercially available or prepared according to patent WO2006/039325A2), (S)-N-methyl-1-phenylethanamine (385 mg, 2.85 mmol) and anhydrous NMP (1 mL) were charged into a microwave tube equipped with a magnetic stirbar. After the vessel was sealed, the mixture was heated at 200° C. for 60 min using microwave irradiation. The reaction was purified by normal phase chromatography (10% CH2Cl2 in hexane then a gradient of 0% to 20% MeOH in CH2Cl2) and by reverse phase chromatography before being lyophilized to give the (S)-N,3-dimethyl-N-(1-phenylethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine (Compound 3) as an off-white solid (69 mg; 36% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.01 (d, J=10.1 Hz, 1H), 7.25-7.39 (m, 6H), 5.71 (q, J=6.9 Hz, 1H), 2.84 (s, 3H), 2.54 (s, 3H), 1.58 (d, J=6.9 Hz, 3H). LRMS [M+H]+: 268 m/z.
Aufarbeitung
- customcommercially available or prepared
- additionwere charged into a microwave tube
- customequipped with a magnetic stirbar
- customAfter the vessel was sealed
- custommicrowave irradiation
- customThe reaction was purified by normal phase chromatography (10% CH2Cl2 in hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-3ccbe63caf7c4db5b8d981dfaa840f58
- Quelldatensatz
- uspto-grants-2016_05
- Patentnummer
- US09328117B2
Verknüpfte Notizen
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