Diisopropylethylamine → HCID 57955610, compound

Participants

Reaction Steps

In a dry round bottom flask, 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid (89.4 mg, 0.2 mmol), 4-((4-methylpiperazin-1-yl)methyl)aniline hydrochloride (66.7 mg, 0.24 mmol) were dissolved in dry N,N-dimethylformamide (3.0 mL). Then added diisopropylethylamine (107 μL, 0.6 mmol) and finally HATU (114 mg, 0.3 mmol) to the reaction, continued at room temperature for 2 hours. After completion, purified the product using reverse phase HPLC using water-acetonitrile solvent system. Pure fractions were mixed and evaporated to a minimal amount then basified with sat.NaHCO3 solution and extracted into EtOAc ((2×100 mL), combined organic layer was washed with sat. brine solution, dried over Na2SO4 and evaporated to get the pure product 72 mg (57% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51-1.80 (m, 6H) 1.97 (br. s., 2H) 2.15 (s, 3H) 2.34 (br. s., 8H) 3.42 (s, 2H) 3.93 (s, 3H) 4.07 (t, J=12 Hz, 2H) 4.80 (t, J=8.21 Hz, 1H) 7.26 (d, J=8.59 Hz, 2H) 7.51-7.67 (m, 2H) 7.70 (m, J=8.59 Hz, 2H) 8.05 (s, 1H) 8.29 (s, 1H) 8.37 (d, J=8.34 Hz, 1H) 10.09 (s, 1H). [M+H] calc'd for C33H40F2N8O3, 635. found 635.

Provenance & Evidence