Tetrahydrofuran → 1-[3-(6-tert-Butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-3-[4-(morpholine-4-carbonyl)-phenylamino]-1H-pyrazole-4-carboxylic acid amide

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Reaction Steps

1-[3-(6-tert-Butyl-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl]-3-[4-(morpholine-4-carbonyl)phenylamino]-1H-pyrazole-4-carbonitrile (52 mg, 0.0861 mmol) was dissolved in 4 mL of THF and 0.4 mL of water. Then dihydrogen tris(dimethylphosphinito)hydroplatinate (CAS#173416-05-2, 3 mg, 8% eq) was added. The mixture was refluxed for 1 hr. TLC indicated complete consumption of the starting material. LC/MS indicated the clean product formed with the correct MW. The mixture was evaporated to dryness and then dissolved in dichloromethane, dried over sodium sulfate and filtered. After the evaporation of solvents, the residue was purified through flash column chromatography (24 g silica gel, methanol in dichloromethane, 0% to 5% in 16 minutes) to give 1-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-3-[4-(morpholine-4-carbonyl)-phenylamino]-1H-pyrazole-4-carboxylic acid amide as a white solid (41 mg, 76.6% yield). LC/MS clacd for C34H35N7O5 (m/e) 621.27, obsd 622.1 (M+H, ES+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.41 (s, 9H) 3.41-3.71 (m, 8H), 4.37 (br. s., 2H), 4.74 (br. s., 1H), 7.36 (d, J=6.3 Hz, 3H), 7.49-7.71 (m, 5H), 7.80 (br. s., 1H), 8.04 (d, J=9.1 Hz, 2H), 8.25 (d, J=6.6 Hz, 1H), 8.56 (br. s., 2H), 9.44 (br. s., 1H).

Provenance & Evidence