HCID 1252891, compound → HCID 85471831, compound

Participants

Reaction Conditions

Reaction Steps

In a 40 mL vial was transferred 2-chloro-5-(furan-2-carboxamido)benzoic acid (I-1) (1 g, 3.75 mmol) in polyphosphoric acid (10 mL), and the 2,3-diamino-5-methyl-pyridine (578 mg, 4.69 mmols, 1.25 eq) was added. The dark brown reaction mixture was heated at 150° C. for 4 hrs. The reaction mixture was then quenched with solid sodium carbonate and extracted with ethyl acetate (3×50 mL). The organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (0-100 EtOAC/Hex), afforded 80 mg (0.22 mmols, 6%) of the title compound (Example 1). 1H NMR (400 MHz, MeOD) δ 8.36-8.25 (m, 1H), 8.20 (s, 1H), 8.04-7.94 (m, 1H), 7.93-7.83 (m, 1H), 7.77 (s, 1H), 7.61 (d, J=8.8 Hz, 1H), 7.31 (d, J=3.5 Hz, 1H), 6.67 (dd, J=1.7, 3.5 Hz, 1H), 2.53 (s, 3H). LCMS M/Z=353.0 (M+1). RT=1.39: Method B.

Provenance & Evidence