4-(2-methylsulfonylethyl)aniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The title compound was prepared following the procedure of example one with N5-(2-Chloro-pyrimidin-4-yl)-1,N5-dimethyl-N2-(4-methyl-benzyl)-1H-benzoimidazole-2,5-diamine (98 mg, 0.25 mmol) and 4-(2-methanesulfonyl-ethyl)-phenylamine (50 mg, 0.25 mmol) as a white solid (104 mg, 70%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 9.05 (s, 1H), 7.70-7.75 (m, 3H), 7.36 (t, J=5.7 Hz, 1H), 7.20-7.29 (m, 3H), 7.07-7.14 (M, 5H), 6.82 (dd, J=8.1 and 1.5 H. 1H), 5.60 (d, J=5.7 Hz, 1H), 4.54 (d, J=5.4 Hz, 2H), 3.57 (s, 3H), 3.42 (s, 3H), 3.30-3.37 (M, 2H), 2.90-2.95 (m, 5H), 2.26 (s, 3H). MS (ESI) m/z=556 [M+H].

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

Procedure: The title compound was prepared following the procedure of example two with N5-(2-Chloro-pyrimidin-4-yl)-1,N5-dimethyl-N2-(1-phenyl-ethyl)-1H-benzoimidazole-2,5-diamine (98 mg, 0.25 mmol) and 4-(2-methanesulfonyl-ethyl)-phenylamine (50 mg, 0.25 mmol) as a white solid (81 mg, 55%). 1H NMR (300 MHz, d6-DMSO) δ 10.09 (s, 1H), 8.87 (s, 1H), 7.84 (d, J=6.9 Hz, 1H), 7.48-7.61 (m, 5H), 7.36-7.40 (m, 3H), 7.20-7.31 (m, 4H), 5.82 (d, J=5.7 Hz, 1H), 5.09 (m, 1H), 3.74 (s, 3H), 3.47 (s, 3H), 3.37-3.42 (M, 2H), 2.94-2.99 (M, 5H), 1.63 (d, J=6.6 Hz, 3H). MS (ESI) m/z=556 [M+H]+.

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

Procedure: The title compound was prepared following the procedure of example two with N5-(2-chloro-pyrimidin-4-yl)-N2-(4-methoxy-benzyl)-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine (82 mg, 0.20 mmol) and 4-(2-Methanesulfonyl-ethyl)-phenylamine (40 mg, 0.20 mmol) as a white solid (57 mg, 47%). 1H NMR (300 MHz, d6-DMSO) δ 9.28 (s, 1H), 7.78 (d, J=6.0 Hz, 1H), 7.67 (d, J=8.4 Hz, 2H), 7.34-7.38 (m, 3H), 7.13-7.18 (m, 3H), 6.94 (d, J=8.4 Hz, 1H), 6.89 (d, J=8.7 Hz, 2H), 5.66 (d, J=6.0 Hz, 1H), 4.57 (d, J=5.4 Hz, 2H), 3.72 (s, 3H), 3.62 (s, 3H), 3.43 (s, 3H), 3.35-3.43 (m, 2H), 2.96 (s, 3H), 2.90-2.96 (m, 2H). MS (ESI) m/z=572 [M+H]+.