To a mixture of [[[4-(2-amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]-acetic acid (50 mg, 0.14 mmol), N-methylbenzylamine (0.022 mL, 0.17 mmol), iPr2NEt (0.07 mL, 0.50 mmol) in DMF (3 mL) was added HATU (68 mg, 0.18 mmol) and stirred at rt overnight. The reaction mixture was poured into ice-water, and the solid was collected by filtration. The solid was re-dissolved in CH2Cl2 and purified by preparative TLC (CH2Cl2-MeOH-Hexane, 8:2:2) affording the product as a light yellow powder. LC-MS: 467 (M++1). 1H NMR (CDCl3): δ 2.92 and 3.00 (each s, 3H), 3.05˜3.12 (m, 4H), 3.62˜3.72 (m, 4H), 4.12˜4.20 (m, 2H), 4.52 and 4.62 (each s, 2H), 5.08 (br.s, 2H), 5.94 (m, 1H), 6.15 (m, 1H), 7.14˜7.24 (m, 3H), 7.26˜7.40 (m, 3H), 7.58˜7.62 (m, 1H), 7.68˜7.72 (m, 1H).
