4'-Methoxy-(1,1'-biphenyl)-4-carboxaldehyde → N1-(isothiazolo[5,4-b]pyrazin-3-yl)-N3-((4'-methoxybiphenyl-4-yl)methyl)propane-1,3-diamine

Participants

Reaction Steps

N1-(Isothiazolo[5,4-b]pyrazin-3-yl)propane-1,3-diamine (410 mg, 1.96 mmol) and 4′-methoxybiphenyl-4-carbaldehyde (410 mg, 1.96 mmol) were combined in 1,2-dichloroethane (8 mL) and treated with sodium triacetoxyborohydride (506 mg, 2.35 mmol). The mixture was shaken at room temperature for 3 h. The reaction was diluted with methylene chloride, quenched with water and the layers were separated. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography, on silica gel, eluting with methylene chloride:methanol to yield N1-(isothiazolo[5,4-b]pyrazin-3-yl)-N3-((4′-methoxybiphenyl-4-yl)methyl)propane-1,3-diamine (100 mg) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): 8.79 (d, 1H), 8.72 (d, 1H), 7.90 (t, 1H), 7.54 (m, 4H), 7.40 (d, 2H), 6.98 (d, 2H), 3.82 (s, 2H), 3.80 (s, 3H), 3.48 (t, 2H), 2.70 (m, 3H), 1.85 ppm (m, 2H). MW=405 confirmed by LC-MS, tr=9.59 min (Method Y) MH+=404-406.

Provenance & Evidence