Reaktion #86374

Reaktionsgleichung

N-ethyl-N-isopropylpropan-2-amine

4-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid

DMF

ammonium chloride

HOBt

EDC

→

TFA

title compound

4-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe crude reaction mixture
2. 2
   Sonstigewas subsequently purified by preparative HPLC
3. 3
   Wascheneluting with a gradient of 30-35% acetonitrile (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6.5 minutes
4. 4
   Sonstigethe solvent removed in vacuo

Vorschrift

To a mixture of 4-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid (0.028 g, 0.091 mmol) in DMF (3 mL) were added ammonium chloride (0.024 g, 0.456 mmol), HOBt (0.018 g, 0.137 mmol), and EDC (0.028 g, 0.146 mmol), followed by N-ethyl-N-isopropylpropan-2-amine (0.079 mL, 0.456 mmol). The reaction mixture was stirred for 18 hours at room temperature. The crude reaction mixture was subsequently purified by preparative HPLC, eluting with a gradient of 30-35% acetonitrile (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6.5 minutes. The product-containing fractions were combined and the solvent removed in vacuo to give a TFA salt of the title compound as an off white solid (0.012 g, 43%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.68 (s, 1H), 7.80 (br s, 1H), 7.95-8.15 (m, 2H), 8.27 (br s, 1H), 8.32-8.47 (m, 2H), 8.81 (d, J=5.05 Hz, 1H), 13.89 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H9F3N4O, 307.1. found 307.11.

Quelle