1-[4-[(3-aminophenyl)methyl]piperazin-1-yl]ethanone

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Chloro-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine (56 mg, 0.22 mmol) and 3-[(4-acetylpiperazin-1-yl)methyl]aniline (142 mg, 0.61 mmol) were mixed and heated neat to 100° C. After 2 hours the reaction was heated to 120° C. for 1 hour then to 140° C. for 1 hour. N,N-di-iso-propylethylamine (0.076 ml, 0.44 mol) was added and the reaction was heated for an additional 1.5 hours. The reaction was cooled, diluted with DMSO and directly purified by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA) to afford the title compound. 1H NMR (300 MHz, CDCl3) δ 8.29 (d, J=5.2 Hz, 1H), 7.67 (d, J=1.5 Hz, 1H), 7.52 (m, 3H), 7.41 (m, 4H), 7.25 (m, 2H), 7.02 (d, J=7.8 Hz, 1H), 6.30 (d, J=5.1 Hz, 1H), 3.63 (t, J=5.5 Hz, 2H), 3.52 (s, 2H), 3.47 (m, 2H), 2.45 (m, 4H), 2.08 (s, 3H). After 2 hours the reaction was heated to 120° C. for 1 hour the reaction was heated for an additional 1.5 hours The reaction was cooled directly purified by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Chloro-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine (56 mg, 0.22 mmol) and 3-[(4-acetylpiperazin-1-yl)methyl]aniline (142 mg, 0.61 mmol) were mixed and heated neat to 100° C. After 2 hours the reaction was heated to 120° C. for 1 hour then to 140° C. for 1 hour. N,N-di-iso-propylethylamine (0.076 ml, 0.44 mol) was added and the reaction was heated for an additional 1.5 hours. The reaction was cooled, diluted with DMSO and directly purified by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA) to afford the title compound. 1H NMR (300 MHz, CDCl3) δ 8.29 (d, J=5.2 Hz, 1H), 7.67 (d, J=1.5 Hz, 1H), 7.52 (m, 3H), 7.41 (m, 4H), 7.25 (m, 2H), 7.02 (d, J=7.8 Hz, 1H), 6.30 (d, J=5.1 Hz, 1H), 3.63 (t, J=5.5 Hz, 2H), 3.52 (s, 2H), 3.47 (m, 2H), 2.45 (m, 4H), 2.08 (s, 3H). After 2 hours the reaction was heated to 120° C. for 1 hour the reaction was heated for an additional 1.5 hours The reaction was cooled directly purified by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA)