Compound 32
8-(((3-(3-(hex-5-yn-1-yl)-3H-diazirin-3-yl)propyl)thio)methyl)-4H-thieno[3,2-c]thiochromene-2-carboxylate 5,5-dioxide
From: A small molecule interacts with VDAC2 to block mouse BAK-driven apoptosis
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Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
To a mixture of intermediate 24 (50 mg, 0.255 mmol, mixture with ~ 20% des-bromo precursor) in MeCN (5 mL) was added the alkyl sulfide 31 followed by K2CO3 (42 mg, 0.306 mmol) and KI (1 crystal, > 1 mg). The mixture was heated to 50 oC for 12 h then cooled to room temperature, concentrated onto silica and purified using ethyl acetate/cyclohexane (20:80) to give 32. Two fractions were obtained both of which appeared to be mixtures of the desired product and methyl sulfone present in the starting material (total of 161 mg approximately 80% of which was the desired product 32 based on 1H NMR). This material was subjected to the next step without further purification. 1H-NMR (300 MHz, CDCl3): δ 1.16-1.23 (m, 2H), 1.33-1.51 (m, 11H), 1.93 (t, J = 2.6 Hz, 1H), 2.12 (td, J = 4.3, 2.6 Hz, 2H), 2.35 (t, J = 14.2 Hz, 2H), 3.74 (s, 2H), 4.35 (q, J = 5.4 Hz, 2H), 4.44 (s, 2H) 7.46 (dd, J = 6.4, 1.6, 1.7 Hz, 1H), 7.60 (s, 1H), 7.68 (s, 1H), 7.97 (d, J = 8.0 Hz, 1H), LCMS: (ES+), m/z = 517 [M+H]+.
