N-{5-[3-(2-chloropyrimidin-4-yl)pyrazolo[1,5-a]pyridin-2-yl]-2-methoxyphenyl}-2-(2-thienyl)acetamide → N-[3-(3-{2-[(7-Amino-5,6,7,8-tetrahydro-2-naphthalenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2-(2-thienyl)acetamide

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Reaction Steps

N-[5-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-(methyloxy)phenyl]-2-(2-thienyl)acetamide (119 mg, 0.25 mmol) and 3-{[2-(dimethylamino)ethyl]oxy}-aniline dihydrochloride (127 mg, 0.50 mmol) were coupled according to the procedure of Example 56, Step H to give the title compound (46 mg, 30%). 1H NMR (400 MHz, d6-DMSO) δ 8.80 (s, 1H), 8.48 (d, J=7.2 Hz, 1H), 8.35 (d, J=9.2 Hz, 1H), 8.16 (d, J=5.2 Hz, 1H), 8.01 (s, 1H), 7.49 (s, 1H), 7.28-7.24 (m, 4H), 7.22-7.18 (m, 1H), 7.12 (d, J=8.4 Hz, 1H), 7.04-7.03 (m, 2H), 6.89-6.86 (m, 2H), 6.61-6.59 (m, 2H), 4.09 (m, 2H), 3.95 (s, 2H), 3.81 (s, 3H), 2.76 (m, 2H), 2.35 (s, 6H) ppm. ES-LC/MS m/z=620 [M+H]+.

Provenance & Evidence