Triethylamine → HCID 86714626, compound

Participants

Reaction Steps

5-(Bromomethyl)isoxazole-3-carboxylic acid (0.718 mmol, 0.148 g) was dissolved in DCM (5 ml) and THF (1 ml). 1,3-Dicyclohexylcarbodiimide (0.718 mmol, 0.148 g) was added and the resulting mixture was stirred at RT. The precipitate formed was filtered and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (0.359 mmol, 0.1 g), triethylamine (0.359 mmol, 0.036 g) and dry DCM (5 ml) was added to the filtrate. The filtrate was stirred at RT under nitrogen atmosphere for two days during which more 1,3-dicyclohexylcarbodiimide (0.148 g), triethylamine (0.050 ml) and 5-(bromomethyl)isoxazole-3-carboxylic acid (0.1 g) were added. The reaction mixture was diluted with DCM and washed with NaHCO3. The organic phase was dried, filtered and evaporated. The crude product was purified with flash chromatography. 0.064 g of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): δ 1.25 (d, 3H), 4.00-4.09 (m, 2H), 4.23-4.31 (m, 1H), 4.41-4.48 (m, 1H), 4.53-4.63 (m, 1H), 6.60-6.66 (m, 1H), 6.74-6.78 (m, 1H), 7.48-7.53 (m, 1H), 7.64 (d, 1H), 7.79-7.88 (m, 2H).

Provenance & Evidence