Compound 7
7-(2-(4-(2-(2-aminoethoxy)ethoxy)benzoyl)phenyl)-N-(4-methylbenzyl)-4H-thieno[3,2-c]thiochromene-2-carboxamide 5,5-dioxide
From: A small molecule interacts with VDAC2 to block mouse BAK-driven apoptosis
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Compound data: NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
To a solution of tert-butyl(2-(2-(4-(2-(2-((4-methylbenzyl)carbamoyl)-5,5-dioxido-4H-thieno[3,2-c]thiochromen-7-yl)benzoyl)phenoxy)ethoxy)ethyl)carbamate (20) (42 mg, 54.8 μmol) in dry DCM was added TFA (83.8 μL, 1.1 mmol). The reaction was monitored by TLC and showed complete conversion after 2 h at room temperature. Reaction mixture was concentrated under vacuum, re-dissolved in methanol then transferred into a SCX column. The crude was washed twice with methanol and then eluted with a 2M ammonia in methanol to give the desired product (30 mg, 92%). 1H-NMR (300 MHz, CDCl3): δ 2.30 (s, 3H), 2.81 (t, J = 5.17 Hz, 2H), 3.50 (t, J = 5.17 Hz, 2H), 3.72-3.79 (m, 2H), 4.06-4.14 (m, 2H), 4.26 (s, 2H), 4.48 (d, J = 5.61 Hz, 2H) 6.76-6.86 (m, 2H), 6.95-7.04 (m, 1H), 7.06-7.12 (m, 2H), 7.14-7.21 (m, 2H), 7.34 (s, 1H), 7.35-7.40 (m, 1H), 7.43-7.53 (m, 5H), 7.55-7.68 (m, 3H), 7.93 (d, J = 1.54 Hz, 1H). 13C-NMR (75 MHz, CDCl3): δ 21.05, 41.53, 43.77, 51.09, 67.56, 69.06, 73.23, 114.27, 124.21, 125.67, 127.87, 128.13, 128.57, 128.81, 128.83, 129.02, 129.37, 129.97, 130.22, 130.57, 132.39, 133.54, 134.28, 134.71, 136.79, 137.34, 138.45, 139.02, 139.21, 141.67, 160.70, 162.89, 196.45. LCMS (ES+), m/z = 667.1 [M+H]+. HRMS (+ESI), m/z = 667.1935[M+H]+ (calculated: 667.1931).
