4-(Prop-2-yn-1-yl)-1lambda~6~,4-thiazinane-1,1-dione → 4-(2-(3-(S,S-dioxo-4-thiapiperidin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

Participants

Reaction Conditions

Reaction Steps

Prepared from 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 6, Step A; 50 mg, 0.13 mmol) and commercially available N-propargyl-S,S-dioxo-4-thiapiperidine (34 mg, 0.19 mmol) according to the procedure described for Example 6, Step B, except the reaction was heated at 50° C. for 5 hours. The crude was purified by preparative TLC [5% MeOH (containing 7N NH3) in CH2Cl2]. The product was obtained as a white powder (45 mg, 67%). 1H NMR (400 MHz, CDCl3) δ 8.49 (d, J=6 Hz, 1H), 7.61 (s, 1H), 7.03 (t, J=9 Hz, 1H), 6.55 (m, 2H), 6.49 (m, 1H), 3.86 (br s, 2H), 3.72 (s, 2H), 3.17 (m, 8H).

Provenance & Evidence