Triethylamine → n-({3-[(4r)-4-(3,3-Dimethylbutyl)-1-hydroxy-4-methyl-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4h-thieno [2,3-e][1,2,4]thiadiazin-7-yl}methyl)methanesulfonamide

Participants

Reaction Steps

A solution of Example 186B (168 mg, 0.36 mmol) in 3 mL of N,N-dimethyl formamide was cooled to 0° C., treated with triethylamine (90 μL, 0.82 mmol) and methanesulfonyl chloride (32 μL, 0.41 mmol), allowed to warm to room temp, stirred for 2 h, diluted with water, and extracted with ethyl acetate. The organic phase was washed with water and concentrated in vacuo to afford a yellow foam. The concentrate was purified on silica gel with a gradient of methanol in dichloromethane (0-2%) to afford the title compound (150 mg, 76% yield). 1H NMR (500 MHz, C6D6) δ ppm 0.40 (m, 1H) 0.72 (s, 9H) 0.82 (m, 1H) 1.55 (s, 3H) 2.01 (m, 1H) 2.21 (td, J=12.66, 3.97 Hz, 1H) 2.97 (s, 3H) 4.28 (d, J=5.49 Hz, 2H) 7.30 (s, 1H) 7.49 (m, 1H) 7.66 (t, J=6.10 Hz, 1H) 7.70 (s, 2H) 8.12 (d, J=7.32 Hz, 1H) 14.42 (m, 1H); MS (APCI−) m/z 550 (M−H)−.

Provenance & Evidence