1-Oxa-2-aza-spiro[4.5]dec-2-ene-3-carbaldehyde → HCID 178422621, compound

Participants

Reaction Conditions

Reaction Steps

1-Oxa-2-aza-spiro[4.5]dec-2-ene-3-carbaldehyde (167 mg, 1.00 mmol, as prepared in Example 19, step B) was placed in a 25 mL round-bottom flask equipped with a magnetic stir bar. 2′-Fluoro-5-methyl-biphenyl-3,4-diamine (218 mg, 1.01 mmol, as prepared in the previous step) was added as a solution in EtOH (10 mL). The flask was fitted with a reflux condenser (top open to air), and the mixture was heated to 80° C. for 6 h. The cooled mixture was concentrated under reduced pressure. The residue was purified by column chromatography using a 40-g SiO2 pre-packed column eluting with EtOAc/hexanes, 0:1 to 3:7, v/v over 30 min, yielding 159 mg (44%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 7.57 (br. s., 1H), 7.50 (td, J=7.8, 1.9 Hz, 1H), 7.31-7.37 (m, 1H), 7.08-7.28 (m, 4H), 2.64 (s, 3H), 2.31 (s, 2H), 1.69-1.89 (m, 6H), 1.47-1.64 (m, 4H).

Provenance & Evidence