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A mixture of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-(5-formyl-3-furyl)-6-methoxy-3-quinolinecarbonitrile (200 mg, 0.43 mmol) and 0.24 mL of N-methylpiperazine (2.2 mmol) in 5 mL of dichloromethane and 1 mL of dimethylformamide is cooled to 0° C. Sodium triacetoxyborohydride (470 mg, 2.22 mmol) is added in portions followed by a few drops of acetic acid. The resulting mixture is stirred at 0° C. for 10 minutes then at room temperature for 5.5 hours. The mixture is partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase is dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash column chromatography eluting with a gradient of 10% methanol in ethyl acetate to 1% ammonium hydroxide in a 1:4 mixture of methanol and ethyl acetate to provide 120 mg (51%) of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6 methoxy-7-{5-[(4-methylpiperazin-1-yl)methyl]-3-furyl}-3-quinolinecarbonitrile as a light yellow solid, mp 179-181° C.; 1H NMR (DMSO-d6) δ 2.15 (s, 3H), 2.23-2.36 (broad s, 4H), 2.38-2.49 (broad s, 4H), 3.54 (s, 2H), 3.87 (s, 3H), 4.06 (s, 3H), 7.01 (s, 1H), 7.33 (s, 1H), 7.74 (s, 1H), 7.94 (s, 1H), 8.10 (s, 1H), 8.28 (s, 1H), 8.43 (s, 1H), 9.82 (s, 1H); MS 552.1, 554.1 (M+H)+; HRMS calcd: 552.15638, found: 552.15599 (M+H)+.

1. waitat room temperature for 5.5 hours
2. customThe mixture is partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
3. dry with materialThe organic phase is dried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue is purified by flash column chromatography
7. washeluting with a gradient of 10% methanol in ethyl acetate to 1% ammonium hydroxide in a 1:4 mixture of methanol and ethyl acetate