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

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To a stirred solution of 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-[3-(1,3-oxazol-5-yl)phenyl]-2-pyrimidinamine (100 mg, 0.22 mmol) in 1 mL THF was added 2-thiopheneacetyl chloride (40 mg, 0.25 mmol). After 15 min. LC/MS indicated the reaction was complete and several equivalents of PS-trisamine were added and the mixture was stirred for 16 h followed by addition of 25 mg of TEA. The mixture was filtered and the resin washed well with THF. The filtrate was concentrated and the crude purified by HPLC (Agilent, 50-90% gradient over 15 min.) to give the title compound (45 mg, 36% yield). 1H NMR (400 MHz, d6-DMSO) δ 10.34 (s, 1H), 9.71 (s, 1H), 8.81 (d, J=6.8 Hz, 1H), 8.49 (d, J=8.6 Hz, 1H), 8.18-8.37 (m, 3H), 7.87 (s, 1H), 7.67-7.72 (m, 2H), 7.54 (s, 1H), 7.24-7.42 (m, 6H), 7.09 (t, J=6.9 Hz, 1H), 6.93-6.95 (m, 2H), 6.49 (d, J=5.3 Hz, 1H), 3.84 (s, 2H) ppm. ES-LC/MS m/z=570 [M+H]+

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