HCID 10820771, compound → Bms-181885

Participants

Reaction Conditions

Reaction Steps

A solution of 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-aminoindole (6) (0.190 g, 0.52 mmol) and 3-(1-methylethoxy)-4-methylcyclobut-3-ene-1,2-dione (3) (0.080 g, 0.52 mmol) in 1 mL of dry DMF was stirred at room temperature for 66 h and then it was heated at 130° C. (oil-bath temperature) for 6 h. The cooled mixture was evaporated and the residue was chromatographed (SiO2/CH2Cl2 --MeOH, 95:5 then CH2Cl2 --MeOH--NH4OH, 95:4.5:0.5 to 90:9:1) to give the title compound (0.138 g, 58%) as a brown foam. This material was treated with excess methanolic HCl, the resulting solution was evaporated and the residue was triturated with isopropanol to give the hydrochloride 0.140 g, 45%) as a solid, mp 200° C. (dec): IR (KBr) 3400, 3220, 1782, 1630, 1600 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ11.08-10.83 (m, 2H), 8.59 (s, 1H), 8.19 (s, 1H), 7.57-7.04 (m, 4H), 4.85 (m, 2H), 3.90 (s, 3H), 2.8-2.4 (m, 8H), 3,13 (m, 2H), 2.26 (s, 1.5H), 2.10 (m, 2H), 1.89 (s, 1.5H). Anal. Calcd for C25H28N6O3. 3 HCl 0.75 H2O. 0.25 C3H8O: C, 51.68; H, 5.81; N, 14.04. Found: C, 51.43; H, 5.61; N, 13.93.

Provenance & Evidence