Potassium sodium tartarate → HCID 46831271, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-indene-5-carboxylate (823 g, 3 mmol) and N(3)-4,5′-bipyrimidin-2-yl-4-methyl benzene-1,3-diamine (973 g, 3.5 mmol) were suspended in 15 mL of toluene, and then a 2 M trimethylaluminium solution (3 mL, 6 mmol) was added. The mixture was stirred overnight at 50° C. and another 2 M trimethylaluminium solution (2 mL, 4 mmol) was added. The solution was stirred overnight at 60° C. and then cooled in an ice bath. Saturated aqueous solution of potassium sodium tartrate was added with stirring. The solution obtained was extracted with methylene chloride (3×100 mL). The pooled extracts were washed with sodium bicarbonate (100 mL) and with brine (2×100 mL), dried over magnesium sulfate, concentrated, and purified by silica gel column chromatography using 50% ethyl acetate/methylene chloride/5-10% triethylamine as eluent to obtain 702 mg of the title compound (45% yield). MS (M+1)=527.27. 1HNMR (DMSO-d6, ppm): δ 10.10 (s, 1H); 9.46 (s, 2H); 9.28 (s, 1H); 9.08 (s, 1H); 8.50 (d, J=5.7 Hz, 1H); 8.04 (s, 1H); 7.74 (s, 1H); 7.70 (d, J=9.0 Hz, 1H); 7.46 (d, J=5.7 Hz, 1H); 7.42 (d, J=9.0 Hz, 1H); 7.32 (d, J=9.0 Hz, 1H); 7.15 (d, J=9.0 Hz, 1H); 4.25 (t, J=5.7 Hz, 1H); 2.2-2.9 (m, 10H); 2.15 (s, 3H); 2.07 (s, 3H); 2.0 (m, 2H).

Provenance & Evidence