(1r)-3-[7-(Azidomethyl)-1,1-dioxido-4h-thieno[2,3-e][1,2,4]thiadiazin-3-yl]-1-(3,3-dimethylbutyl)-4-hydroxy-1-methylnaphthalen-2(1h)-one → (1r)-3-[7-(Aminomethyl)-1,1-dioxido-4h-thieno[2,3-e][1,2,4]thiadiazin-3-yl]-1-(3,3-dimethylbutyl)-4-hydroxy-1-methylnaphthalen-2(1h)-one

Participants

Reaction Steps

A solution of Example 186A (17 mg, 0.03 mmol) in 2 mL of ethanol was degassed, treated with palladium on carbon (˜1 mg, 10%), put under an atmosphere of hydrogen, stirred for 4 h at room temp, filtered through a plug of celite, and concentrated to afford a yellow solid. The crude material was chromatographed on silica gel with a gradient of methanol in dichloromethane (0-10%) to afford the title compound (8.2 mg, 51% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.44 (m, 1 H) 0.70 (s, 9 H) 0.79 (m, 1 H) 1.39 (s, 3 H) 1.74 (m, J=3.31 Hz, 1 H) 2.15 (td, J=12.41, 4.23 Hz, 1 H) 4.12 (s, 2 H) 7.22 (s, 1 H) 7.33 (m, 1 H) 7.48 (m, 2 H) 8.04 (d, J=7.35 Hz, 1 H) 8.17 (br. s., 2 H) 16.99 (s, 1 H); MS (APCI+) m/z 474 (M+H)+.

Provenance & Evidence