1-Phenethylamine → 3-Methyl-N-(1-phenylethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine

HRID 521556

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.[C:12]1([CH:18]([NH2:20])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CN1C(=O)CCC1>CO.O>[CH3:11][C:8]1[N:6]2[N:7]=[C:2]([NH:20][CH:18]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH3:19])[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine (200 mg, 1.186 mmol; commercially available or prepared according to patent WO2006/039325A2), rac-1-phenylethanamine (575 mg, 4.75 mmol; commercially available from Aldrich) and anhydrous NMP (1 mL) were charged into a microwave tube equipped with a magnetic stirbar (light brown solution). After the vessel was sealed, the mixture was heated at 150° C. for 15 min, followed by an extra 45 min using microwave irradiation. The reaction was then diluted with MeOH/H2O (19:1), filtered, purified by reverse phase chromatography and lyophilized to give the rac-3-methyl-N-(1-phenylethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine (Compound 1) as a white solid (42 mg; 14% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.84 (d, J=9.8 Hz, 1H), 7.81 (d, J=7.1 Hz, 1H), 7.42 (d, J=7.8 Hz, 2H), 7.32 (t, J=7.5 Hz, 2H), 7.21 (t, J=7.3 Hz, 1H), 6.80 (d, J=9.8 Hz, 1H), 4.92 (dd, J=7.0, 7.0 Hz, 1H), 2.42 (s, 3H), 1.49 (d, J=6.9 Hz, 3H). LRMS [M+H]+: 254 m/z.

Aufarbeitung

customcommercially available or prepared
customequipped with a magnetic stirbar (light brown solution)
customAfter the vessel was sealed
custommicrowave irradiation
filtrationfiltered
custompurified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag: ord-3f58149dc3cc4665a2ee64382ade9437
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09328117B2

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