3-chloro-N-propan-2-ylpropane-1-sulfonamide

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

Procedure: To a solution of 8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio-9H-purin-6-amine (39 mg, 0.09 mmol) in DMF (2 mL) was added 3-chloro-N-isopropylpropane-1-sulfonamide (100 mg, 0.45 mmol) and Cs2CO3 (62 mg, 0.19 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was condensed under vacuum and the residue was purified by Prep TLC (CH2Cl2:NH3-MeOH (7N), 20:1) to yield WS54 as a white solid (14 mg, 26%). 1H NMR (500 MHz, CDCl3/MeOH-d4): δ 8.00 (s, 1H), 7.19 (s, 1H), 6.86 (s, 1H), 5.86 (s, 2H), 4.17 (t, J=7.3 Hz, 2H), 3.34 (septet, J=6.6 Hz, 1H), 2.89 (t, J=7.6 Hz, 2H), 2.05-2.13 (m, 2H), 0.99 (d, J=6.6 Hz, 6H); HRMS (ESI) m/z [M+H]+ calcd. for C15H22IN6O4S2, 577.0189. found 577.0194. condensed under vacuum the residue was purified by Prep TLC (CH2Cl2:NH3-MeOH (7N), 20:1)

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

Procedure: To a solution of 8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio-9H-purin-6-amine (39 mg, 0.09 mmol) in DMF (2 mL) was added 3-chloro-N-isopropylpropane-1-sulfonamide (100 mg, 0.45 mmol) and Cs2CO3 (62 mg, 0.19 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was condensed under vacuum and the residue was purified by Prep TLC (CH2Cl2:NH3-MeOH (7N), 20:1) to yield WS54 as a white solid (14 mg, 26%). 1H NMR (500 MHz, CDCl3/MeOH-d4): δ 8.00 (s, 1H), 7.19 (s, 1H), 6.86 (s, 1H), 5.86 (s, 2H), 4.17 (t, J=7.3 Hz, 2H), 3.34 (septet, J=6.6 Hz, 1H), 2.89 (t, J=7.6 Hz, 2H), 2.05-2.13 (m, 2H), 0.99 (d, J=6.6 Hz, 6H); HRMS (ESI) m/z [M+H]+ calcd. for C15H22IN6O4S2, 577.0189. found 577.0194. condensed under vacuum the residue was purified by Prep TLC (CH2Cl2:NH3-MeOH (7N), 20:1)

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

Procedure: To a solution of 8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio-9H-purin-6-amine (39 mg, 0.09 mmol) in DMF (2 mL) was added 3-chloro-N-isopropylpropane-1-sulfonamide (100 mg, 0.45 mmol) and Cs2CO3 (62 mg, 0.19 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was condensed under vacuum and the residue was purified by Prep TLC (CH2Cl2:NH3-MeOH (7N), 20:1) to yield WS54 as a white solid (14 mg, 26%). 1H NMR (500 MHz, CDCl3/MeOH-d4): δ 8.00 (s, 1H), 7.19 (s, 1H), 6.86 (s, 1H), 5.86 (s, 2H), 4.17 (t, J=7.3 Hz, 2H), 3.34 (septet, J=6.6 Hz, 1H), 2.89 (t, J=7.6 Hz, 2H), 2.05-2.13 (m, 2H), 0.99 (d, J=6.6 Hz, 6H); HRMS (ESI) m/z [M+H]+ calcd. for C15H22IN6O4S2, 577.0189. found 577.0194. condensed under vacuum the residue was purified by Prep TLC (CH2Cl2:NH3-MeOH (7N), 20:1)