2-Thiopheneacetyl chloride → N-[3-(3-{2-[(4-chloro-3-{[2-(1-pyrrolidinyl)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2-(2-thienyl)acetamide

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Reaction Steps

The title compound was prepared from 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(4-chloro-3-{[2-(1-pyrrolidinyl)ethyl]oxy}phenyl)-2-pyrimidinamine and 2-thiopheneacetyl chloride using acylation conditions described in Example 1, Step F, and purification via column chromatography using a 0-20% gradient of EtOAc/MeOH w/NH4OH to generate the product in 71% yield. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.7 (s, 4H) 3.8 (s, 3H) 4.0 (s, 3H) 6.5 (s, 1H) 6.9 (d, J=4.4 Hz, 2H) 7.1 (t, J=6.9 Hz, 2H) 7.2 (t, J=9.0 Hz, 2H) 7.4 (m, 3H) 7.5 (m, 2H) 7.7 (s, 2H) 7.9 (s, 1H) 8.2 (d, J=0.9 Hz, 1H) 8.4 (s, 1H) 8.8 (d, J=1.3 Hz, 1H) 9.7 (s, 1H) 10.3 (s, 1H). ES-LC/MS m/z 650 [M+H]+.

Provenance & Evidence