Reaction Steps
A solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (302 mg, 0.760 mmol), benzenesulfonyl chloride (0.12 mL, 0.94 mmol), and Et3N (0.15 mL, 1.1 mmol) in CH2Cl2 (7.5 mL) was heated at reflux for 17 h, then concentrated in vacuo. The residue was partitioned between saturated NaHCO3(aq) (15 mL) and EtOAc (20 mL). The aqueous phase was extracted with EtOAc (20 mL), and the combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (400:5:1 CH2Cl2/MeOH/NH4OH) afforded AMD9830 (229 mg, 71%) as a yellow foam. 1H NMR (CDCl3) δ 1.64-2.03 (m, 3H), 2.37 (m, 1H), 2.66-2.84 (m, 2H), 3.76-3.89 (m, 4H), 4.06 (m, 1H), 4.41 (dd, 1H, J=9.6, 6.0 Hz), 4.66 (d, 1H, J=15 Hz), 4.79 (d, 1H, J=15 Hz), 6.76 (d, 2H, J=8.1 Hz), 7.07 (m, 1H), 7.18 (d, 2H, J=8.1 Hz, 7.27 (m, 2H), 7.41 (m, 3H), 7.55 (m, 5H), 7.84 (m, 3H), 7.96 (m, 2H), 8.48 (m, 1H); 13C NMR (CDCl3) δ 20.15, 27.15, 27.55, 45.30, 51.78, 53.32, 61.49, 111.81, 118.60, 119.84, 122.59, 123.06, 125.43, 125.60, 127.06, 127.47, 127.76, 131.01, 131.24, 131.92, 132.55, 132.69, 134.81, 136.75, 138.13, 139.21, 140.14, 145.11, 151.74, 156.99. ES-MS m/z 678 (M+H). Anal. Calcd. for C37H35N5S2O4.0.5H2O: C, 64.70; H, 5.28; N, 10.20. Found: C, 64.65; H, 5.11; N, 10.08.
