Triethylamine → HCID 57513780, compound

Participants

Reaction Steps

A 100 mL rbf was charged DCM (14.29 ml) followed by addition of 2-amino-N-(1-benzyl-5-(4-fluorophenyl)-1H-1,2,4-triazol-3-yl)-2-methylpropanamide (1.000 g, 2.83 mmol) and (S)-1-methylpyrrolidine-2-carboxylic acid (0.402 g, 3.11 mmol). And it was stirred at room temperature for 10 min, the clear solution save for a couple of particles, was placed in an ice bath at 2° C. Then HATU (2.152 g, 5.66 mmol) and triethylamine (0.789 ml, 5.66 mmol) were added. The yellow semi-solution was allowed to stir at 2° C. for 5 h. It was allowed to warm to room temperature over night. It was diluted with DCM (25 mL) and H2O (30 mL). The white precipitates were collected by filtration and washed with 1:1 water/sat. NaHCO3 solution. (2×60 mL), brine (2×40 mL). This afforded the title compound 1H NMR (400 MHz, DMSO-d6) d ppm 1.53 (d, J=1.52 Hz, 6H) 1.66-1.78 (m, 3H) 1.96-2.13 (m, 1H) 2.21-2.29 (m, 1H) 2.30 (s, 3H) 2.61-2.70 (m, 1H) 2.99-3.09 (m, 1H) 5.43 (s, 2H) 7.13 (d, J=6.95 Hz, 2H) 7.26-7.43 (m, 5H) 7.68-7.75 (m, 2H) 7.97 (s, 1H) 10.21 (s, 1H). Theoretical mass 464.23. found 464.23. MS (m/z) 465.00 M (+1), tR=1.23, Meth A. ee: 95%, using 30% EtOH Heptane.

Provenance & Evidence