2-(1-acetylpiperidin-4-yl)ethyl 4-methylbenzenesulfonate

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

Procedure: The title compound was prepared by a similar procedure described for step 7 of example 1 using 2-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-1H-imidazo[4,5-c]pyridin-4-amine and 2-(1-acetylpiperidin-4-yl)ethyl 4-methylbenzenesulfonate. 1H NMR (DMSO-d6) δ; 7.70 (d, J=6.0 Hz, 1H), 7.38 (s, 1H), 6.79 (d, J=6.0 Hz, 1H), 6.66 (s, 1H), 6.42 (s, 2H), 6.07 (s, 2H), 4.30 (brd, J=13.2 Hz, 1H), 4.20 (t, J=7.2 Hz, 2H), 3.74 (brd, J=13.2 Hz, 1H), 2.89 (t, J=13.6 Hz, 1H), 2.40 (t, J=13.6 Hz, 1H), 1.96 (s, 3H), 1.66 (m, 2H), 1.56-1.51 (m, 2H), 1.43 (m, 1H), 1.08 (m, 1H), 0.94 (m, 1H); LC-MS [M+H]+ 518.09.

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

Procedure: The title compound was prepared by a similar procedure described for step 7 of example 1 using 2-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-1H-imidazo[4,5-c]pyridin-4-amine and 2-(1-acetylpiperidin-4-yl)ethyl 4-methylbenzenesulfonate. 1H NMR (DMSO-d6) δ; 7.70 (d, J=6.0 Hz, 1H), 7.38 (s, 1H), 6.79 (d, J=6.0 Hz, 1H), 6.66 (s, 1H), 6.42 (s, 2H), 6.07 (s, 2H), 4.30 (brd, J=13.2 Hz, 1H), 4.20 (t, J=7.2 Hz, 2H), 3.74 (brd, J=13.2 Hz, 1H), 2.89 (t, J=13.6 Hz, 1H), 2.40 (t, J=13.6 Hz, 1H), 1.96 (s, 3H), 1.66 (m, 2H), 1.56-1.51 (m, 2H), 1.43 (m, 1H), 1.08 (m, 1H), 0.94 (m, 1H); LC-MS [M+H]+ 518.09.

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

Procedure: To a suspension of 8-bromoadenine (0.042 g, 0.197 mmol) and toluene-4-sulfonic 2-(1-acetyl-piperidin-4-yl)-ethyl ester (0.077 g, 0.237 mmol) in THF was added Barton's base (50 μl, 0.237 mmol) at room temperature. The reaction mixture was heated at 100° C. for 15 min in microwave reactor, at the end of this period reaction was cooled to room temperature and the crude was purified by Isco silica gel flash column using 0-5% gradient of methanol in dichloromethane to give 0.030 g (42%) of 9-[2-(1-acetylpiperidin-4-yl)-ethyl]-8-bromo-9H-purin-6-amine, LC-MS [M+H]+ 366.2 and 0.015 g (21%) of 3-[2-(1-acetylpiperidin-4-yl)-ethyl]-8-bromo-3H-purin-6-amine, LC-MS [M+H]+ 366.2 was cooled to room temperature the crude was purified by Isco silica gel flash column

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

Procedure: To a suspension of 8-bromoadenine (0.042 g, 0.197 mmol) and toluene-4-sulfonic 2-(1-acetyl-piperidin-4-yl)-ethyl ester (0.077 g, 0.237 mmol) in THF was added Barton's base (50 μl, 0.237 mmol) at room temperature. The reaction mixture was heated at 100° C. for 15 min in microwave reactor, at the end of this period reaction was cooled to room temperature and the crude was purified by Isco silica gel flash column using 0-5% gradient of methanol in dichloromethane to give 0.030 g (42%) of 9-[2-(1-acetylpiperidin-4-yl)-ethyl]-8-bromo-9H-purin-6-amine, LC-MS [M+H]+ 366.2 and 0.015 g (21%) of 3-[2-(1-acetylpiperidin-4-yl)-ethyl]-8-bromo-3H-purin-6-amine, LC-MS [M+H]+ 366.2 was cooled to room temperature the crude was purified by Isco silica gel flash column

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

Procedure: The title compound was prepared by a similar procedure described for step 7 of example 1 using 2-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-1H-imidazo[4,5-c]pyridin-4-amine and 2-(1-acetylpiperidin-4-yl)ethyl 4-methylbenzenesulfonate. 1H NMR (DMSO-d6) δ; 7.70 (d, J=6.0 Hz, 1H), 7.38 (s, 1H), 6.79 (d, J=6.0 Hz, 1H), 6.66 (s, 1H), 6.42 (s, 2H), 6.07 (s, 2H), 4.30 (brd, J=13.2 Hz, 1H), 4.20 (t, J=7.2 Hz, 2H), 3.74 (brd, J=13.2 Hz, 1H), 2.89 (t, J=13.6 Hz, 1H), 2.40 (t, J=13.6 Hz, 1H), 1.96 (s, 3H), 1.66 (m, 2H), 1.56-1.51 (m, 2H), 1.43 (m, 1H), 1.08 (m, 1H), 0.94 (m, 1H); LC-MS [M+H]+ 518.09.

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

Procedure: To a suspension of 8-bromoadenine (0.042 g, 0.197 mmol) and toluene-4-sulfonic 2-(1-acetyl-piperidin-4-yl)-ethyl ester (0.077 g, 0.237 mmol) in THF was added Barton's base (50 μl, 0.237 mmol) at room temperature. The reaction mixture was heated at 100° C. for 15 min in microwave reactor, at the end of this period reaction was cooled to room temperature and the crude was purified by Isco silica gel flash column using 0-5% gradient of methanol in dichloromethane to give 0.030 g (42%) of 9-[2-(1-acetylpiperidin-4-yl)-ethyl]-8-bromo-9H-purin-6-amine, LC-MS [M+H]+ 366.2 and 0.015 g (21%) of 3-[2-(1-acetylpiperidin-4-yl)-ethyl]-8-bromo-3H-purin-6-amine, LC-MS [M+H]+ 366.2 was cooled to room temperature the crude was purified by Isco silica gel flash column

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

Procedure: To a suspension of 8-bromoadenine (0.042 g, 0.197 mmol) and toluene-4-sulfonic 2-(1-acetyl-piperidin-4-yl)-ethyl ester (0.077 g, 0.237 mmol) in THF was added Barton's base (50 μl, 0.237 mmol) at room temperature. The reaction mixture was heated at 100° C. for 15 min in microwave reactor, at the end of this period reaction was cooled to room temperature and the crude was purified by Isco silica gel flash column using 0-5% gradient of methanol in dichloromethane to give 0.030 g (42%) of 9-[2-(1-acetylpiperidin-4-yl)-ethyl]-8-bromo-9H-purin-6-amine, LC-MS [M+H]+ 366.2 and 0.015 g (21%) of 3-[2-(1-acetylpiperidin-4-yl)-ethyl]-8-bromo-3H-purin-6-amine, LC-MS [M+H]+ 366.2 was cooled to room temperature the crude was purified by Isco silica gel flash column