3-(Pyrrolidin-1-ylmethyl)aniline → 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-fluorophenyl}-2-(2-thienyl)acetamide (100 mg, 0.22 mmol) and 3-(1-pyrrolidinylmethyl)aniline (78 mg, 0.44 mmol) were coupled according to the procedure of Example 56, Step H to give of the title compound (35 mg, 26%). 1H NMR (400 MHz, d6-DMSO) δ 10.11 (s, 1H), 9.49 (s, 1H), 8.80 (d, J=6.8 Hz, 1H), 8.44 (d, J=8.8 Hz, 1H), 8.26-8.22 (m, 2H), 7.64 (s, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.43 (t, J=7.8 Hz, 1H), 7.37-7.32 (m, 3H), 7.16-7.07 (m, 2H), 6.95-6.93 (m, 2H), 6.85 (d, J=7.2 Hz, 1H), 6.49 (d, J=4.8 Hz, 1H), 3.96 (s, 2H), 3.48 (br s, 2H), 2.38 (m, 4H), 1.64 (m, 4H) ppm. ES-LC/MS m/z=604 [M+H]+.

Provenance & Evidence