Hydrochloric Acid → HCID 67348795, compound

Participants

Reaction Steps

Obtained as a by-product during hydrogenation of the alkyne of 4-(2-(3-(diethylamino)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline (Example 6, Step B). A mixture of N-4-(2-(3-(diethylamino)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine (Example 6, Step B; 106 mg, 0.287 mmol), 4N HCl in dioxane (72 μL, 0.29 mmol), palladium on carbon (61 mg, 0.029 mmol; Degussa type, 10 wt % Pd. 50% water), and 1:1 CH2Cl2/EtOH (10 mL) was purged with N2 (3×), and then shaken under H2 (50 psi) for 18 hours at room temperature on a Parr shaker. The mixture was filtered, rinsing the Pd/C with MeOH. The resulting filtrate was concentrated, and the residue was partitioned between EtOAc (20 mL) and a saturated aqueous solution of NaHCO3 (20 mL). The phases were separated, and the aqueous phase was re-extracted with EtOAc (2×10 mL). The combined organic phases were washed with brine (10 mL), dried (Na2SO4), filtered, and concentrated. The crude was purified by preparative TLC (25% MeOH in CH2Cl2). The product was obtained as a waxy solid (8 mg, 8%). 1H NMR (400 MHz, CDCl3) δ 8.41 (m, 1H), 7.23 (s, 1H, overlaps with chloroform), 7.03 (m, 1H), 6.52 (m, 3H), 3.81 (br s, 2H), 2.93 (m, 2H), 1.80 (m, 2H), 1.03 (m, 3H).

Provenance & Evidence