Sodium Carbonate → N'-Hydroxy-2-{3-[2-(trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboximidamide
Reaktionsgleichung
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:16]#[N:17])=[CH:14][N:15]=2)[CH2:7]1.Cl.[NH2:25][OH:26].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[OH:26][N:25]=[C:16]([C:13]1[S:12][C:11]([N:8]2[CH2:9][CH2:10][CH:6]([O:5][C:4]3[CH:18]=[CH:19][CH:20]=[CH:21][C:3]=3[C:2]([F:23])([F:1])[F:22])[CH2:7]2)=[N:15][CH:14]=1)[NH2:17]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
A mixture of 2-{3-[2-(trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carbonitrile (370 mg, 1.1 mmol), hydroxylamine hydrochloride (303 mg, 4.4 mmol) and sodium carbonate (231 mg, 2.2 mmol) in EtOH—H2O (4:1, 20 mL) was heated at 80° C. for 2 h. Solvent was evaporated in vacuo. The residue was diluted with H2O, extracted three times with EtOAc, dried (Na2SO4) and concentrated. Trituration with hexanes:Et2O (1:1) gave the title compound as white powder. 1H NMR (400 MHz, acetone-d6): δ 8.73 (s, 1 H), 7.66 (m, 2 H), 7.52 (s, 1 H), 7.38 (d, 1 H), 7.16 (t, 1 H), 5.46 (m, 3 H), 3.94-3.88 (m, 1 H), 3.75-3.59 (m, 3 H), 2.56-2.30 (m, 2 H).
Aufarbeitung
- customSolvent was evaporated in vacuo
- additionThe residue was diluted with H2O
- extractionextracted three times with EtOAc
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-15b49b863db84f06a30a9588e801531f
- Quelldatensatz
- uspto-grants-2010_07
- Patentnummer
- US07754745B2
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