Ethyl hydrogen (4-{[4-({2-(diethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → Ethyl hydrogen (3-fluoro-4-{[4-({6-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

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Reaction Steps

Prepared analogously to Compound 3A using diethyl (3-fluoro-4-{[4-({6-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)pyridin-3-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate (Compound 22B, 156 mg, 230 μmol) to afford 141 mg of the title compound (94%). 1H NMR (400 MHz, CD3OD) δ=9.05 (d, J=4.8 Hz, 1H), 8.55 (s, 1H), 8.32 (s, 1H), 8.23 (s, 1H), 7.71 (d, J=8.8 Hz, 1H), 7.50 (t, J=7.8 Hz, 1H), 7.26 (d, J=11.9 Hz, 1H), 7.17 (d, J=8.3 Hz, 1H), 4.31 (t, J=6.8 Hz, 2H), 3.88 (quin, J=7.0 Hz, 2H), 3.58 (t, J=6.1 Hz, 2H), 3.05 (d, J=21.0 Hz, 2H), 2.96-3.00 (m, 3H), 2.11 (quin, J=6.5 Hz, 2H), 1.13 (t, J=7.1 Hz, 3H). MS (ESI): m/z=653.66 [M+H]+. UPLC: tR=1.09 min (UPLC-SQD: analytical—2 min).

Provenance & Evidence