Reaction Steps
the intermediate from above (121 mg, 0.26 mmol) was converted to the hydrobromide salt with simultaneous deprotection of the BOC group to afford 89 mg (79%) of AMD9361 as a white solid. 1H NMR (D2O) □1.84 (s, 3H), 2.02-2.11 (m, 2H), 2.27-2.35 (m, 1H), 2.44-2.53 (m, 1H), 2.93-3.08 (m, 2H), 4.02 (d, 1H, J=12 Hz), 4.30 (d, 1H, J=12 Hz), 4.50 (s, 2H), 4.75 (s, 2H), 7.50-7.60 (m, 5H), 7.93 (dd, 1H, J=8, 1 Hz), 8.05-8.10 (m, 1H), 8.15 (d, 1H, J=8 Hz), 8.57-8.63 (m, 2H), 8.87 (br d, 1H, J=6 Hz); 13C NMR (D2O) □18.5, 25.7, 27.8, 31.2, 46.2, 47.7, 51.7, 62.6, 125.5, 128.1, 128.4, 131.3, 131.6, 133.1, 136.4, 142.2, 144.4, 145.6, 146.4, 147.1, 150.6. ES-MS m/z 373 (M+H). Anal. Calcd. for C24H28N4.4.6HBr.1.8H2O: C, 37.09; H, 4.69; N, 7.21; Br, 47.30. Found: C, 36.99; H, 4.68; N, 6.99; Br, 47.43. AMD9405: Preparation of N-(2-pyridinylmethyl)-N′-(1H-benzimidazol-2-ylmethyl)-N′-(8-methyl-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (free base)
