Reaktion #86386

Reaktionsgleichung

6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid

HOBt

EDC

2-aminoethanol

N-ethyl-N-isopropylpropan-2-amine

→

title compound

Ausbeute 36.3%

N-(2-hydroxyethyl)-6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinamide

Ausbeute 36.3%

Lösungsmittel

EtOAc

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwas washed with brine
2. 2
   SonstigeVolatiles were evaporated from the organic phase
3. 3
   Sonstigethe residue was purified by CombiFlash® chromatography
4. 4
   Wascheneluting with a gradient of 0-20% MeOH in DCM
5. 5
   Einengenconcentrated in vacuo

Vorschrift

To 6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid (1.6 g, 4.98 mmol) in DMF (20 mL) were added HOBt (0.942 g, 6.97 mmol), EDC (1.432 g, 7.47 mmol), 2-aminoethanol (0.913 g, 14.94 mmol), followed by N-ethyl-N-isopropylpropan-2-amine (4.34 mL, 24.90 mmol). The reaction mixture was stirred for 16 hours at room temperature, was subsequently diluted with EtOAc and was washed with brine. Volatiles were evaporated from the organic phase and the residue was purified by CombiFlash® chromatography, eluting with a gradient of 0-20% MeOH in DCM. The product-containing fractions were combined and concentrated in vacuo to give the title compound as a white solid (0.658 g, 36.3%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.43 (s, 3H), 3.44 (q, J=5.98 Hz, 2H), 3.57 (t, J=5.94 Hz, 2H), 7.38-7.44 (m, 1H), 7.90-8.07 (m, 4H), 8.70 (t, J=5.81 Hz, 1H); ESI-MS m/z [M+H]+ calc'd for C17H15F3N4O2, 365.1. found 365.2.

Quelle