Bicarbonate Ion → HCID 71542133, compound

Participants

Reaction Steps

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (228 mg, 0.775 mmol) was added to a solution of 5-chloro-2-pyridinecarboxylic acid (122 mg, 0.775 mmol) in MeOH (0.6 mL), followed by a solution of (S)-3-bromo-5′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,4′-[1,3]oxazine]-2′,7-diamine (140 mg, 0.388 mmol) in THF (1.6 mL) MeOH (0.5 mL). The reaction mixture was allowed to stir for 20 min at rt. Diluted, aqueous bicarbonate solution was added, followed by additional water and EtOAc. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica gel, 20-100% EtOAc/hexanes). 40 mg of (S)—N-(2′-amino-3-bromo-5′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,4′-[1,3]oxazin]-7-yl)-5-chloropicolinamide were obtained as an off-white solid. MS m/z=501.7 [M+H]11. Calculated for C21H15BrClN5O3: 500.73. 1H NMR (300 MHz, CHLOROFORM-d) ppm 1.82-1.93 (m, 1H) 1.93-2.02 (m, 1H) 4.07-4.19 (m, 1H) 4.19-4.32 (m, 1H) 7.31 (d, J=8.62 Hz, 1H) 7.71 (d, J=2.48 Hz, 1H) 7.73-7.79 (m, 1H) 7.89 (dd, J=8.33, 2.34 Hz, 1H) 7.93 (d, J=2.48 Hz, 1H) 8.26 (d, J=8.33 Hz, 1H) 8.31 (d, J=2.48 Hz, 1H) 8.58 (d, J=1.90 Hz, 1H) 9.86 (s, 1H).

Provenance & Evidence