Diisopropylethylamine → HCID 71542704, compound

Participants

Reaction Steps

The (S)-3-bromo-5′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,4′-[1,3]oxazine]-2′,7-diamine (0.035 g, 0.097 mmol) was dissolved in MeOH (2 mL) and 4-chloro-2-fluorobenzoic acid (0.019 g, 0.107 mmol) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride hydrate (0.031 g, 0.107 mmol) were added, followed by N-ethyl-N-isopropylpropan-2-amine (0.019 mL, 0.107 mmol). After 35 min, additional 4-chloro-2-fluorobenzoic acid (0.0095 g, 0.053 mmol) and additional 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride hydrate (0.015 g, 0.053 mmol) were added. After 2 h, the reaction was taken up in EtOAc (75 mL), and the organic layer was washed with half-saturated NaHCO3 (2×10 mL), then with saturated brine (10 mL), dried over MgSO4 and concentrated. The material was purified by preparative tlc (85% EtOAc-hexane) to afford (S)—N-(2′-amino-3-bromo-5′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,4′-[1,3]oxazin]-7-yl)-4-chloro-2-fluorobenzamide (9.7 mg, 0.019 mmol). MS (m/z) 517/519 (M+H)+. 1H NMR (400 MHz, CDCl3): 8.40 (d, 1H, J=14.7 Hz), 8.31 (d, 1H, J=2.4 Hz), 8.12 (t, 1H, J=8.5 Hz), 7.91 (d, 1H, J=2.4 Hz), 7.62 (m, 2H), 7.31 (m, 1H), 7.27 (m, 1H), 7.23 (m, 1H), 4.21 (m, 1H), 4.11 (m, 1H), 1.94 (m, 1H), 1.85 (m, 1H).

Provenance & Evidence