Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylate → HCID 86618696, compound

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Prepared from tert-butyl 4-{[6-(aminomethyl)pyridin-2-yl]oxy}piperidine-1-carboxylate (629 mg, 2.05 mmol) and 5-(4-chloro-phenyl)-3-(dimethylamino-methyleneamino)-thiophene-2-carboxylic acid methyl ester (662 mg, 2.05 mmol) according to the procedure in Example 14c. Purification by silica gel flash chromatography using a 40+M Biotage column with a gradient of 10-100% EtOAc in heptane yielded the title compound as a colorless solid. Yield: 679 mg (60%). 1H NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 7.60 (m, 2H), 7.53 (t, 1H, J=7.7 Hz), 7.46 (s, 1H), 7.39 (m, 2H), 6.95 (d, 1H, J=7.2 Hz), 6.60 (d, 1H, J=8.2 Hz), 5.18 (s, 2H), 4.96 (m, 1H), 3.66 (m, 2H), 3.09 (m, 2H), 1.78 (m, 2H), 1.56 (m, 2H), 1.41 (s, 9H).

Provenance & Evidence