Diisopropylethylamine → 6-Chloro-2H-chromene-3-carboxylic acid (Quinolin-4-ylmethyl)-amide

Participants

Reaction Steps

To a vial containing 6-chloro-2H-chromene-3-carboxylic acid (43.74 mg, 0.21 mmol) was added a solution containing N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (79 mg, 0.21 mmol), DIPEA (2.4 eq), and 4-dimethylaminopyridine (2.1 mg, 0.017 mmol) in anhydrous DMF (3 mL). After stirring for 5 minutes, a solution of quinolin-4-yl-methylamine dihydrochloride (40 mg, 0.2 mmol) and DIPEA (2.4 eq) in anhydrous DMF (2 mL) was added. The reaction was stirred overnight at room temperature. The reaction mixture was poured into saturated NaHCO3 solution (50 mL) and extracted with EtOAc (3×50 mL). The combined organics were washed with brine (3×50 mL), dried (MgSO4), filtered and concentrated. Flash chromatography (0 to 4% MeOH in DCM over 30 minutes) gave the product (26.4 mg) as a solid. m/z=350.8 (M+1), r.t.=2.26 mins. 1H NMR (400 MHz; DMSO-d6) δ 8.99 (1H, t), 8.86 (1H, d), 8.20 (1H, dd), 8.06 (1H, dd), 7.79 (1H, t), 7.67 (1H, t), 7.42 (1H, d), 7.34 (2H, d), 7.27 (1H, dd), 6.90 (1H, d), 5.00 (2H, s), 4.90 (2H, d).

Provenance & Evidence