Diisopropylethylamine → HCID 131731685, compound

Participants

Reaction Conditions

Reaction Steps

To a 20 ml vial were added (S)-2-amino-3-(4-chlorophenyl)-N-(3-(pyridin-4-yl)isoxazol-5-yl)propanamide 3.1.C (50 mg, 0.15 mmole), thiazole-4-carbaldehyde (20 mg, 0.18 mmole), sodium triacetoxyborohydride (62 mg, 0.29 mmole), 5 ml of DCE, and DIEA (97 μl, 0.15 mmole). The reaction was stirred at 70° C. for 12 hours. The reaction was then partitioned between 10 ml of water and 20 ml of DCM and the solvent was removed by rotary evaporation. The crude was purified using reverse phase preparative HPLC to give 5.55 mg of (S)-3-(4-chlorophenyl)-N-(3-(pyridin-4-yl)isoxazol-5-yl)-2-(thiazol-4-ylmethylamino)propanamide TFA salt 3.1 as a clear film (5.6 mg, 9% yield). LCMS ESI (pos.) m/e: 440.1 (M+1): 1H NMR (500 MHz, MeOH) δ ppm 9.01 (d, J=1.71 Hz, 1H), 8.76-8.78 (m, 2H), 8.19 (d, J=6.60 Hz, 2H), 7.69 (dd, J=13.82, 8.68 Hz, 1H), 7.24 (d, J=1.96 Hz, 1H), 7.13 (d, J=8.31 Hz, 2H), 6.99 (d, J=8.31 Hz, 2H), 4.35-4.45 (s, 1H), 4.26 (m, 2H), 3.34 (dd, J=8.56, 5.87 Hz, 1H), 3.17 (dd, J=13.69, 5.87 Hz, 1H).

Provenance & Evidence