1H-Benzotriazole, 1-hydroxy-, ammonium salt (1:1) → HCID 178425238, Verbindung

Temperatur

25 °C

A mixture of 5-methyl-1-(1-phenylethyl)-1H-pyrazole-4-carboxylic acid (49 mg, 0.21 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (95 mg, 0.5 mmol), N-hydroxybenzotrizole (67 mg, 0.5 mmol), triethylamine (0.1 mL) and dichloromethane (5 mL) was stirred at 25° C. for 0.5 hours. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (50 mg, 0.33 mmol) was added. The mixture was stirred at 25° C. for 12 hours. To the mixture, water (10 ml) was added and the mixture was extracted with dichloromethane (10 mL×3). The combined organic phase was dried by sodium sulfate and then filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-5-methyl-1-(1-phenylethyl)-1H-pyrazole-4-carboxamide as a white solid (43 mg, 56%). LRMS (M+H+) m/z: calcd 364.19. found 364. 1H NMR (300 MHz, d6-DMSO): δ 11.46 (s, 1H), 8.34 (s, 1H), 7.70 (t, J=5.1 Hz, 1H), 7.35-7.18 (m, 5H), 5.84 (s, 1H), 5.49 (q, J=7.2 Hz, 1H), 4.20 (d, J=4.8 Hz, 2H), 2.29 (s, 3H), 2.15 (s, 3H), 2.10 (s, 3H), 1.73 (d, J=6.9 Hz, 3H).

1. stirringThe mixture was stirred at 25° C. for 12 hours
2. extractionthe mixture was extracted with dichloromethane (10 mL×3)
3. dry with materialThe combined organic phase was dried by sodium sulfate
4. filtrationfiltered
5. concentrationThe filtrate was concentrated in vacuo
6. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

ORD-Eintrag

ord-d8c5dbceac2949208dd71999492802ce

Quelldatensatz

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09085583B2