4-Morpholinobenzaldehyde → HCID 178514001, compound

Participants

Reaction Conditions

Reaction Steps

(1S,2R,3S,4R)-3-(2,3-diamino-5-chloropyridin-4-ylamino)-7-oxabicyclo[2.2.1]heptane-2-carboxamide (17) (300 mg, 0.971 mmol), and 4-morpholinobenzaldehyde (167 mg, 0.873 mmol) were taken in EtOH (15 ml) to which ammonium acetate (112 mg) was added and the reaction mixture was heated at 70° C. for 48 h. Crude LCMS showed the desired product along with trace of starting material. The reaction mixture was allowed to come to rt and the precipitated was filtered and washed well with hot ethanol to afford the desired product (466 mg, 23%) as a yellow solid. NMR: δ (1H, 400M Hz, DMSO-d6): 1.50-1.80 (4H, m), 2.96 (1H, d, J=8.4 Hz), 3.23 (4H, s), 3.76 (4H, s), 4.33 (1H, d, J=4.5 Hz), 4.57 (1H, s), 5.49 (1H, t, J=8.8 Hz), 6.99 (1H, d, J=8.4 Hz), 7.08 (1H, d, J=8.4 Hz), 7.18 (1H, s), 7.62 (1H, s), 7.91 (1H, s), 8.02 (1H, d, J=8.0 Hz), 12.96 (1H, s). LCMS (254 nm): [M+H]+ 469.15 (95.56%) HPLC: 91.64% (220 nm).

Provenance & Evidence