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Reaction of pyridine-2-carboxylic acid 4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzylamide (AMD9397) (40 mg, 0.11 mmol), 1H-benzoimidazole-2-carbaldehyde (16 mg, 0.11 mmol), and NaBH(OAc)3 (68 mg, 0.32 mmol) for 2 h at 60° C. followed by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH 198:1:1) gave AMD9401 (28 mg, 52%) as a white foam. 1H NMR (300 MHz, CD3OD) δ 1.60-1.63 (m, 1H), 1.95-2.06 (m, 2H), 2.20-2.22 (m, 1H), 2.66-2.83 (m, 2H), 3.51 (d, 1H, J=13.2 Hz), 3.58 (d, 1H, J=13.2 Hz), 3.94 (d, 1H, J=15.3 Hz), 4.04-4.09 (m, 3H), 4.42 (br s, 2H), 7.09-7.15 (m, 4H), 7.20 (dd, 1H, J=7.8, 4.8 Hz), 7.20 (d, 1H, J=8.1 Hz), 7.28 (d, 2H, J=8.1 Hz), 7.41-7.47 (m, 2H), 7.48-7.52 (m, 2H), 7.91 (ddd, 1H, J=7.5, 7.5, 1.8 Hz), 8.06 (d, 1H, J=7.8 Hz), 8.55 (d, 1H, J=4.5 Hz), 8.60 (d, 1H, J=4.5 Hz); 13C NMR (75.5 MHz, CD3OD) δ 22.84, 24.33, 30.62, 44.13, 51.41, 56.15, 63.13, 123.55, 124.03, 128.13, 128.61, 130.80, 137.39, 138.95, 139.14, 139.51, 139.67, 148.35, 150.17, 151.40, 156.31, 158.31, 166.94. ES-MS m/z 503 (M+H). Anal. Calcd. for C31H30N6O.0.8H2O.0.3CH2Cl2: C, 69.30; H, 5.98; N, 15.49. Found: C, 69.63; H, 6.14; N, 15.19.
