Hydrochloric Acid → HCID 178519584, Verbindung

HRID 2401987Notizen

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([F:21])[CH:16]=3)[S:12][C:11]=2[C:22]2[N:26]=[CH:25][N:24](C3CCCCO3)[N:23]=2)[OH:9])=[CH:4][CH:3]=1.C(O)(C)(C)C.O1CCOCC1.Cl.C(=O)(O)[O-].[Na+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([F:21])[CH:16]=3)[S:12][C:11]=2[C:22]2[NH:26][CH:25]=[N:24][N:23]=2)[OH:9])=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A mixture of (4-Chlorophenyl){5-(2-fluoropyridin-4-yl)-2-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-3-thienyl}methanol (0.261 g, 0.554 mmol), tert-butyl alcohol (3.9 mL, 41 mmol), 1,4-dioxane (2.6 mL, 33 mmol) and 4.00 M HCl in dioxane (3.66 mL, 16.6 mmol) was heated at 70° C. for 2 h. The mixture was cooled down. A small amount of water was added, followed by the addition of sodium bicarbonate (0.745 g, 8.87 mmol). The mixture was stirred for 10 min and then evaporated in vacuum. The residue was purified by (HPLC to afford 4-chlorophenyl)[5-(2-fluoropyridin-4-yl)-2-(4H-1,2,4-triazol-3-yl)-3-thienyl]methanol as a white solid. LCMS: (AA) ES+ 387.2, 389.1; 1H NMR (300 MHz, d4-methanol) δ: 8.51 (s, 1H), 8.18 (d, J=5.41 Hz, 1H), 7.73 (s, 1H), 7.60-7.44 (m, 3H), 7.37-7.23 (m, 3H), 6.76 (s, 1H).

Aufarbeitung

temperatureThe mixture was cooled down
customevaporated in vacuum
customThe residue was purified by (HPLC to afford 4-chlorophenyl)[5-(2-fluoropyridin-4-yl)-2-(4H-1,2,4-triazol-3-yl)-3-thienyl]methanol as a white solid

Quellen und Nachweise

ORD-Eintrag: ord-48e86bf52933498bb0de15c943b17514
Quelldatensatz: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08796271B2

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