Tris(hydroxymethyl)aminomethane → N-{5-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-methylphenyl}-2-(2-thienyl)acetamide

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Reaction Steps

To a solution of 5-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-methylaniline (856 mg, 2.55 mmol) in THF (25 mL) was added thiophene-2-acetyl chloride (0.33 mL, 2.68 mmol). When TLC showed the reaction to be complete, PS-trisamine was added. After 16 h, TEA was added and the mixture was filtered. The filtrate was diluted with DCM and washed with water. The organic phase was dried over MgSO4 and concentrated onto silica gel. The crude material was purified by column chromatography to give of the desired product (1.13 g, 97%). 1H NMR (400 MHz, d6-DMSO) δ 9.63 (s, 1H), 8.87 (d, J=7.2 Hz, 1H), 8.43-8.39 (m, 2H), 7.70 (s, 1H), 7.62 (t, J=8.0 Hz, 1H), 7.38-7.30 (m, 3H), 7.20 (m, 1H), 7.18 (d, J=6.8 Hz, 1H), 7.09-6.95 (m, 2H), 3.91 (s, 2H), 2.28 (s, 3H) ppm.

Provenance & Evidence