1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(3-fluoro-4-(1-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

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Reaction Steps

Prepared according to the procedure for Example 2, Step A, substituting 3-fluoro-4-(1-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)benzenamine (22 mg, 0.085 mmol; obtained from Example 3, Step C) for 4-(1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine. In addition, the amount of EDCI (94 mg, 0.51 mmol) and ((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid (117 mg, 0.51 mmol) were both increased. The crude was purified by preparative TLC eluting with EtOAc. The product was obtained as a white solid (1.4 mg, 3%). LRMS (ESI+): 97% purity, 220 nm, m/z 464 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 10.0 (br s, 1H), 8.35 (d, J=5 Hz, 1H), 8.10 (s, 1H), 7.78 (m, 1H), 7.76 (s, 1H), 7.45 (m, 2H), 7.23 (m, 1H), 7.07 (m, 2H), 6.41 (d, J=5 Hz, 1H), 4.14 (s, 3H), 1.81 (m, 2H), 1.62 (m, 2H).

Provenance & Evidence