(1-(Prop-2-yn-1-yl)piperidin-4-yl)methanol → N-(3-fluoro-4-(2-(3-(4-(hydroxymethyl)piperidin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

Participants

Reaction Steps

Prepared from N-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (Example 12, Step A, 20 mg, 0.0338 mmol) and (1-(prop-2-ynyl)piperidin-4-yl)methanol (10.4 mg, 0.0676 mmol) using the procedure described for Example 6, Step B. The crude was purified by preparative TLC (1 mm thickness, Rf=0.72) eluting with 20% MeOH/DCM. The product was obtained as a beige powder (6.7 mg, 32%). HPLC: 100% purity (220 nm); LRMS (APCI+): 100% purity, 220 nm, m/z 617 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 10.14 (s, 1H), 8.48 (d, J=5 Hz, 1H), 8.42 (s, 1H), 7.75 (m, 1H), 7.59 (s, 1H), 7.47 (m, 2H), 7.28 (m, 1H), 7.21 (m, 1H), 7.05 (t, J=9 Hz, 2H), 6.52 (d, J=5 Hz, 1H), 3.65 (s, 2H), 3.53 (d, J=6 Hz, 2H), 3.09 (m, 2H), 2.38 (m, 2H), 1.86 (m, 2H), 1.81 (m, 2H), 1.64 (m, 2H), 1.55 (m, 1H), 1.45 (m, 2H).

Provenance & Evidence