1-Hydroxybenzotriazole → 4-[3-(3-Chloro-4-isopropoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-pyridine
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:5]([NH:7][OH:8])=[NH:6].[CH3:16][C:17]1[CH:25]=[N:24][CH:23]=[CH:22][C:18]=1[C:19](O)=O.C1C=CC2N(O)N=NC=2C=1.N=C=N.C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:19]([C:18]3[CH:22]=[CH:23][N:24]=[CH:25][C:17]=3[CH3:16])[O:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14]Komponenten
7
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 160 °C
Versuchsvorschrift
To a microwave vial charged with 3-chloro-N-hydroxy-4-isopropoxy-benzamidine (75 mg, 0.328 mmol), 3-methyl-isonicotinic acid (41 mg, 0.298 mmol), HOBt (46 mg, 0.298 mmol), PS-carbodiimide (720 mg, 0.894 mmol, loading 1.24 mmol/g) was added acetonitrile (3.5 mL) and diisopropylethylamine (156 μL, 0.894 mmol). The reaction vial was capped and heated at about 160° C. for about 30 minutes in a Biotage microwave. The reaction mixture was filtered and the resin was washed with acetonitrile (4 mL). Filtrate was concentrated to dryness. The crude product was purified via reverse phase HPLC (30-90% acetonitrile, 30 minute ramp) to give 10.2 mg (10%) of 4-[3-(3-chloro-4-isopropoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-pyridine.
Aufarbeitung
- customThe reaction vial was capped
- filtrationThe reaction mixture was filtered
- washthe resin was washed with acetonitrile (4 mL)
- concentrationFiltrate was concentrated to dryness
- customThe crude product was purified via reverse phase HPLC (30-90% acetonitrile, 30 minute ramp)
Quellen und Nachweise
- ORD-Eintrag
- ord-4dc39e01fa6242ba936217e2a406435d
- Quelldatensatz
- uspto-grants-2010_11
- Patentnummer
- US07834039B2
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