1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18516856, compound

Participants

Reaction Steps

A solution of N-3-aminophenyl-5-cyano-4-thien-2-ylpyrimidine-2-amine (300 mg, 1.0 mmol) and 4-(4-methylpiperazin-1-yl)methylbenzoic acid, lithium salt (300 mg, 1.0 mmol) in DMF (10 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (307 mg, 1.6 mmol), 1-hydroxybenzotriazole (216 mg, 1.6 mmol) and N-methylmorpholine (350 ml, 3.2 μmol) and the resulting mixture was stirred at ambient temperature for 48 h. The reaction was then concentrated under reduced pressure and the resulting residue partitioned between ethyl acetate and saturated brine. The organic phase was dried (MgSO4), concentrated under reduced pressure and the resulting residue recrystallised from ethyl acetate-ether-MeOH (4:4:1) to give the title compound (312 mg) as a colourless solid, m.p. 208-209°. δH (d6 DMSO) 10.48 (1H, bs), 10.23 (1H, s), 8.89 (1h,s), 8.28 (1H, d, J 3.5 Hz), 8.13 (1H, m), 7.98 (1H, d, J 4.8 Hz), 7.90 (2H, d, J 8.2 Hz), 7.60 (1H, bs), 7.43 (3H, d, J 8.2 Hz), 7.36-7.30 (2H, s), 3.52 (2H, s), 2.37 (8H, bs) and 2.15 (3H,s).

Provenance & Evidence