Dimethylamine → 5-{5-[3-(3-Dimethylamino-propoxy)-phenylamino]-2-methylphenyl}-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrile

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Reaction Steps

To a solution of methanesulfonic acid 3-{3-[3-(4-cyano-5-methylsulfanyl-3-pyridin-3-yl-thiophene-2-yl)-4-methyl-phenylamino]-phenoxyl}-propyl ester (20 mg, 0.035 mmol) in DCM (1 mL) was added excess dimethylamine and excess triethylamine. The reaction was stirred at ambient temperature for 3 hours then water (2 ml) was added and the product extracted with DCM (3 mL×3). The combined organic layer were concentrated to afford the crude product as an oil. Purification by chromatography (2% MeOH—CH2Cl2) afforded the desired product (17 mg, 95%). 1H NMR (CDCl3): δ 8.6 (d, 1H), 8.5 (s, 1H), 8.1 (s, 1H), 7.7 (d, 1H), 7.4–7.0 (m, 4H), 7.0 (d, 1H), 6.5 (d, 1H), 4.1 (t, 2H), 2.9 (m, 2H), 2.7 (s, 3H), 2.6 (s, 6H), 2.1 (m, 2H), 1.6 (s, 3H).

Provenance & Evidence