Triethylamine → HCID 178493835, compound

Participants

Reaction Steps

5-Amino-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-ol bis(trifluoroacetate) (500 mg, 1.1 mmol) was diluted in DCM (10 mL), and triethylamine (0.75 mL, 5.4 mmol) was added. The suspension was stirred at rt for 1.5 h, after which time 5-amino-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-ol trifluoroacetate was isolated. The compound, thus prepared, (1.1 mmol) was dissolved in DMF (10 mL). Cesium carbonate (1.41 g, 4.3 mmol) and Intermediate C (218 mg, 1.1 mmol) were added, and the mixture was stirred at 70° C. for 30 min. Additional Intermediate C (109 mg, 0.55 mmol) and cesium carbonate (350 mg, 1.1 mmol) were added, and stirring was continued for 1 h. Another aliquot of Intermediate C (109 mg, 0.55 mmol) was added, and the temperature was increased to 75° C. After 3 h, the reaction mixture was cooled to rt and filtered through a pad of Celite, washing with methanol and DCM. The filtrate was concentrated under reduced pressure, dry loaded onto silica gel, and purified by biotage eluting with 5-10% methanol in DCM followed by 5-15% methanolic ammonia (2.0 M, Aldrich) in DCM. The resultant oil was triturated with a 1:1 mixture of hexanes:EtOAc (15 mL) to afford the desired as a solid (171 mg, 44%): HPLC MS RT=1.07 min, MH+=360.3; 1H NMR (DMSO-d6) δ: 7.43 (1H, d), 6.73 (3H, m), 4.03 (2H, t), 3.88 (4H, m), 3.69 (3H, s), 3.55 (4H, m), 2.42 (2H, t), 2.35 (4H, m), 1.87 (2H, m).

Provenance & Evidence