4-(2-methylpropyl)piperidin-4-ol

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

Procedure: To a mixture of 4-isobutylpiperidin-4-ol (70 mg, 0.44 mmol), 4-(2-aminoquinoline-8-sulfonamido)benzoic acid (100 mg, 0.44 mmol), and HBTU (134 mg, 0.53 mmol) in DCM (5 mL) was added DIPEA (1 mL) dropwise at room temperature, and then the mixture was stirred at room temperature for 1 hour. The resulting mixture was concentrated, purified by a standard method to yield the title compound. 1H NMR (CHLOROFORM-d) δ: 8.10-8.20 (m, 1H), 7.89 (d, J=9.1 Hz, 1H), 7.69-7.82 (m, 1H), 7.06-7.26 (m, 5H), 6.80 (d, J=9.1 Hz, 1H), 5.41 (s, 2H), 4.33 (br. s., 1H), 3.41-3.19 (m., 3H), 1.82 (dt, J=12.9, 6.4 Hz, 1H), 1.63-1.46 (m, 4H), 1.40 (d, J=5.9 Hz, 2H), 0.97 (d, J=6.7 Hz, 6H). LCMS (m/z): 483.7 (M+1)+ The resulting mixture was concentrated purified by a standard method

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

Procedure: To a mixture of 4-isobutylpiperidin-4-ol (70 mg, 0.44 mmol), 4-(2-aminoquinoline-8-sulfonamido)benzoic acid (100 mg, 0.44 mmol), and HBTU (134 mg, 0.53 mmol) in DCM (5 mL) was added DIPEA (1 mL) dropwise at room temperature, and then the mixture was stirred at room temperature for 1 hour. The resulting mixture was concentrated, purified by a standard method to yield the title compound. 1H NMR (CHLOROFORM-d) δ: 8.10-8.20 (m, 1H), 7.89 (d, J=9.1 Hz, 1H), 7.69-7.82 (m, 1H), 7.06-7.26 (m, 5H), 6.80 (d, J=9.1 Hz, 1H), 5.41 (s, 2H), 4.33 (br. s., 1H), 3.41-3.19 (m., 3H), 1.82 (dt, J=12.9, 6.4 Hz, 1H), 1.63-1.46 (m, 4H), 1.40 (d, J=5.9 Hz, 2H), 0.97 (d, J=6.7 Hz, 6H). LCMS (m/z): 483.7 (M+1)+ The resulting mixture was concentrated purified by a standard method

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

Procedure: To a mixture of 4-isobutylpiperidin-4-ol (70 mg, 0.44 mmol), 4-(2-aminoquinoline-8-sulfonamido)benzoic acid (100 mg, 0.44 mmol), and HBTU (134 mg, 0.53 mmol) in DCM (5 mL) was added DIPEA (1 mL) dropwise at room temperature, and then the mixture was stirred at room temperature for 1 hour. The resulting mixture was concentrated, purified by a standard method to yield the title compound. 1H NMR (CHLOROFORM-d) δ: 8.10-8.20 (m, 1H), 7.89 (d, J=9.1 Hz, 1H), 7.69-7.82 (m, 1H), 7.06-7.26 (m, 5H), 6.80 (d, J=9.1 Hz, 1H), 5.41 (s, 2H), 4.33 (br. s., 1H), 3.41-3.19 (m., 3H), 1.82 (dt, J=12.9, 6.4 Hz, 1H), 1.63-1.46 (m, 4H), 1.40 (d, J=5.9 Hz, 2H), 0.97 (d, J=6.7 Hz, 6H). LCMS (m/z): 483.7 (M+1)+ The resulting mixture was concentrated purified by a standard method