Dimethylamine → HCID 86689958, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(3-(3-(4-(bis(2-chloroethyl)amino)phenyl)ureido)phenyl)-2-chloroacetamide (0.88 g, 2 mmol) in THF (50 mL) was added dropwise dimethylamine (2M solution in THF) (2 mL, 4.0 mmol). The reaction mixture was heated at 50-60° C. for overnight. After cooling the mixture, the solvent was removed by evaporation under reduced pressure. The residue obtained was triturated with saturated aqueous solution of NaHCO3. The solid product was collected by filtration, washed successively with water and hexane, and dried to yield N-(3-(3-(4-(bis(2-chloroethyl)amino)phenyl)ureido)phenyl)-2-(dimethyl-amino)acetamide (BO-2189), 0.56 g (62%), mp 62-64° C. The product was dissolved in ethanol and excess of HCl in ethylacetate was added. The solution was evaporated in vacuo to dryness and the residue was co-evaporated several times with EtOH to dryness to form BO-2189 hydrochloride. 1H NMR (DMSO-d6) δ: 2.88 (6H, s, CH3), 3.68-3.71 (8H, m, CH2), 4.13 (2H, s, CH2), 6.71-6.73 (2H, d, J=8.8 Hz, Ar—H), 7.16-7.30 (5H, m, Ar—H), 7.78 (1H, s, Ar—H), 8.95 (1H, brs, NH), 9.24 (1H, brs, NH), 9.99 (1H, brs, NH). 13C NMR (CDCl3, 125 MHz) δ: 41.09, 43.25, 52.73, 57.88, 108.84, 112.56, 113.17, 113.55, 120.03, 129.04, 138.31, 140.73, 152.86, 162.91. HRMS [ES+]: calcd for C21H27Cl2N5O2, 452.3774 [M+H]+. found 452.1620. HPLC 97.3%.

Provenance & Evidence