Triethylamine → 3-Chloro-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)propane-1-sulfonamide

Participants

Reaction Steps

A solution of Example 186B (64 mg, 0.14 mmol) in 1.5 mL of N,N-dimethyl formamide was cooled to 0° C., treated with triethylamine (30 μL, 0.28 mmol) and 3-chloropropylsulfonyl chloride (19 μL, 0.15 mmol), stirred for 30 minutes, 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 solid. This crude material was purified by chromatography on silica gel with a gradient of methanol in dichloromethane (0-2%) to afford the title compound as a pale compound (42 mg, 64%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.39 (td, J=12.8, 3.5 Hz, 1H), 0.72 (s, 9H), 0.82 (m, 1H), 1.56 (s, 3H), 2.13 (m, 4H), 3.21 (m, 2H), 3.75 (t, J=6.4 Hz, 2H), 4.28 (d, J=5.9 Hz, 2H), 7.33 (s, 1H), 7.51 (m, 1H), 7.72 (m, 2H), 7.90 (t, J=6.3 Hz, 1H), 8.13 (d, J=7.7 Hz, 1H), 14.09 (s, 1H); MS (APCI−) m/z 612 (M−H)−; Anal calc'd for C26H32ClN3O6S3: C, 50.84; H, 5.25; N, 6.84. found: C, 51.07; H, 5.28; N, 6.51.

Provenance & Evidence