3-(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:

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 1 with N5-(2-Chloro-pyrimidin-4-yl)-N2-cyclohexyl-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine (74 mg, 0.20 mmol) and 3-(2-methanesulfonyl-ethyl)-phenylamine (47 mg, 0.20 mmol) as a white solid (59 mg, 52%). 1H NMR (300 MHz, D6-DMSO) δ 9.07 (s, 1H), 7.76-7.78 (m, 2H), 7.60 (d, J=8.4 Hz, 1H), 7.13-7.20 (m, 2H), 7.09 (d, J=1.8 Hz, 1H), 6.79-6.82 (m, 2H), 6.47 (d, J=7.8 Hz, 1H), 5.61 (d, J=6.0 Hz, 1H), 3.70 (m, 1H), 3.51 (s, 3H), 3.44 (s, 3H), 3.35-3.40 (m, 2H), 2.97 (s, 3H), 2.91-2.95 (m, 2H), 2.01 (m, 2H), 1.74 (M, 2H), 1.63 (m, 1H), 1.16-1.31 (m, 5H) ppm. MS (ESI) m/z=534 [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 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 3-(2-methanesulfonyl-ethyl)-phenylamine (50 mg, 0.25 mmol) as a white solid (126 mg, 85%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 9.07 (s, 1H), 7.75-7.77 (m, 2H), 7.59 (d, J=8.1 Hz, 1H), 7.36 (t, J=6.0 Hz, 1H), 7.07-7.29 (M, 7H), 6.79-6.85 (M, 2H), 5.61 (d, J=5.7 Hz, 1H), 4.54 (d, J=5.7 Hz, 2H), 3.57 (s, 3H), 3.43 (s, 3H), 3.32-3.40 (m, 2H), 2.97 (s, 3H), 2.90-2.97 (M, 2H), 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 3-(2-methanesulfonyl-ethyl)-phenylamine (50 mg, 0.25 mmol) as a white solid (48 mg, 32%). 1H NMR (300 MHz, d6-DMSO) δ 9.08 (s, 1H), 7.73-7.77 (m, 2H), 7.58 (d, J=8.4 Hz, 1H), 7.44 (d, J=7.5 Hz, 2H), 7.29-7.34 (m, 2H), 7.12-7.23 (m, 4H), 7.05 (d, J=1.5 Hz, 1H), 6.79-6.84 (m, 2H), 5.59 (d, J=5.7 Hz, 1H), 5.14 (m, 1H), 3.60 (s, 3H), 3.41 (s, 3H), 3.32-3.41 (m, 2H), 2.90-2.96 (m, 5H), 1.53 (d, J=6.9 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 3-(2-Methanesulfonyl-ethyl)-phenylamine (40 mg, 0.20 mmol) as a white solid (69 mg, 57%). 1H NMR (300 MHz, ds-DMSO) δ 9.08 (s, 1H), 7.76 (d, J=6.0 Hz, 2H), 7.59 (d, J=8.4 Hz, 1H), 7.28-7.34 (m, 3H), 7.08-7.23 (m, 3H), 6.79-6.89 (m, 4H), 5.61 (d, J=5.7 Hz, 1H), 4.52 (d, J=5.7 Hz, 2H), 3.72 (s, 3H), 3.55 (s, 3H), 3.43 (s, 3H), 3.35-3.40 (M, 2H), 2.97 (s, 3H), 2.90-2.94 (m, 2H). MS (ESI) m/z=572 [M+H]+.