Oxalyl chloride → HCID 67542121, compound

Participants

Reaction Steps

Oxalyl chloride (63.46 μL; 0.75 mmol) was added to suspension of example 4 (97.10 mg; 0.25 mmol) and DMF (0.50 μL; 0.01 mmol) in DCM (10 mL) and the resulting mixture was stirred at RT for 1 hour. The solution was then evaporated to dryness, the residue taken up in THF (3 mL) and then added to a mixture of glycine methyl ester hydrochloride salt (FLUKA; 50110; 31.39 mg; 0.25 mmol) and DIEA (189.56 μL; 1.10 mmol) in THF (2 mL). The reaction mixture was stirred at RT for 2 hours, filtered through a SPE NH2 column (2 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography (c-hex/EtOAc: 9.5/0.5), affording the title compound as a yellow oil (99 mg; 86%). 1H NMR (DMSO-d6, 300 MHz) δ 8.95-8.90 (m, 1H), 8.18 (br s, 1H), 8.10-8.04 (m, 2H), 7.98 (dd, J=10.8, 1.3 Hz, 1H), 7.93-7.88 (m, 1H), 7.40-7.27 (m, 4H), 7.15-7.12 (m, 1H), 4.07 (d, J=5.5 Hz, 2H), 3.69 (s, 3H), 2.14 (s, 3H), 2.04 (s, 3H). LC/MS (Method B): 458.5 (M−H)−, 460.3 (M+H)+. HPLC (Method A) Rt 5.57 min (Purity: 99.2%).

Provenance & Evidence