Reaktion #1996311

Reaktionsgleichung

sodium chloride salt

2-(2-hydroxypropan-2-yl)-6-(4-methylphenyl)pyridine-4-carboxylic acid

(1S)-1-(4H-1,2,4-triazol-3-yl)ethanamine

triethylamine

EDC

→

hydrogen chloride

title compound

2-(2-Hydroxypropan-2-yl)-6-(4-methylphenyl)-N-[(1S)-1-(4H-1,2,4-triazol-3-yl)ethyl]pyridine-4-carboxamide

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was cooled to ambient temperature
2. 2
   Sonstigethe mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Vorschrift

To a solution of the sodium chloride salt of 2-(2-hydroxypropan-2-yl)-6-(4-methylphenyl)pyridine-4-carboxylic acid (224 mg, 0.58 mmol) in DMF (2.3 mL) was added the hydrochloride salt of (1S)-1-(4H-1,2,4-triazol-3-yl)ethanamine (160 mg, 0.87 mmol), HOST (89 mg, 0.58 mmol), triethylamine (322 pt, 2.31 mmol), and EDC (139 mg, 0.72 mmol). The resulting mixture was heated to 60° C. After 30 min, the mixture was cooled to ambient temperature. A small amount of water was added and the mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid). Treatment with 2 M hydrogen chloride in diethyl ether gave the title compound as the hydrochloride salt. (230 mg). HRMS 366.1920 (M+1). 1H NMR (399 MHz, DMSO): δ 9.28 (d, J=7.9 Hz, 1H); 8.38 (s, 1H); 8.18 (s, 1H); 8.07 (d, J=8.0 Hz, 2H); 8.02 (d, J=1.3 Hz, 1H); 7.33 (d, J=7.9 Hz, 2H); 5.37 (t, J=7.3 Hz, 1H); 2.38 (s, 3H); 1.59 (d, J=7.0 Hz, 3H); 1.52 (s, 6H).

Quelle