1,2-Dichloroethane → HCID 44256263, compound

Participants

Reaction Steps

A suspension of 3-(4-(2-phenylacetamido)phenyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acid (59A) (14 mg, 0.038 mmol), EDC (9 mg, 0.047 mmol) and HOBt (6.4 mg, 0.047 mmol) in a mixed solvent of DMF (0.5 mL) and DCM (0.5 mL) was stirred for 5 min, and then (S)-2-aminobutan-1-ol hydrochloride salt (5.6 mg, 0.045 mmol) and triethylamine (7.6 mg, 0.075 mmol) were added. The mixture was stirred at room temperature overnight. The solvent was removed in vacuo. The crude product was purified by preparative HPLC using CH3CN/H2O/TFA solvent system to yield the title compound (8.3 mg, 50%). HPLC/MS (Method C): retention time 1.75, [M+H]+=444.5. 1H NMR (500 MHz, DMSO-d6): δ 10.50 (s, 1H), 9.58 (d, J=8.25 Hz, 1H), 8.71 (d, J=7.15 Hz, 1H), 8.14 (d, J=6.05 Hz, 1H), 7.80-7.92 (m, 4H), 7.30-7.43 (m, 4H), 7.26 (t, J=6.60 Hz, 1H), 7.19 (t, J=6.87 Hz, 1H), 3.93-4.07 (m, 1H), 3.71 (s, 2H), 3.54-3.63 (m, 1H), 3.50 (dd, J=11.0 Hz, 4.95 Hz, 1H), 1.68-1.78 (m, 1H), 1.54-1.65 (m, 1H), 0.87-1.06 (m, 3H).

Provenance & Evidence