Ethanol → HCID 178511914, compound

Participants

Reaction Steps

To an argon purged round bottom flask containing compound 39 (153 mg, 0.529 mmol) was added 10% by weight palladium on carbon (56 mg, 0.053 mmol) and a magnetic stirbar, followed by the addition of absolute ethanol (10 mL). The system was fitted with a hydrogen filled balloon. The argon atmosphere was removed using a water aspirator and replaced with hydrogen. The atmosphere was removed twice more and replaced with hydrogen a total of 3 times and was stirred for 17.5 hours. TLC (2M NH3 in methanol:CH2Cl2, 5:95) revealed the reaction was complete. The reaction was filtered through a 5 um PTFE frit. The frit washed with absolute ethanol (5 mL). The filtrate was transferred to a reaction vial fitted with a magnetic stirbar, and was purged with argon. Methyl thiophene-2-carbimidothioate hydroiodide (226 mg, 0.793 mmol) was added as a solid and the reaction was stirred at room temperature for 18 hours. The reaction was complete by TLC and was diluted with ether (40 mL) and the reaction was filtered to collect the precipitate. The precipitate washed with ether. The precipitate was dissolved in ethanol and stirred at room temperature with DOWES-66 resin (3.00 g). The mixture was stirred at room temperature for 2 hours. The reaction was filtered and the filtrate concentrated. The material was purified by silica gel column chromatography (2M NH3 in methanol:CH2Cl2, 2.5:97.5 to 5:95) to obtain compound 40 (122 mg) as a brown oil. 1H NMR (DMSO-d6) δ 7.72 (d, J=3.6 Hz, 1H), 7.58 (d, J=3.6 Hz, 1H), 7.41 (d, J=8.7 Hz, 1H), 7.29 (d, J=3.0 Hz, 1H), 7.09 (t, J=4.5 Hz, 1H), 6.97 (s, 1H), 6.69 (d, J=9.0 Hz, 1H), 6.32 (d, J=3.0 Hz, 1H), 6.22 (brs, 2H), 4.17 (t, J=6.6 Hz, 2H), 3.58 (t, J=4.5 Hz, 4H), 2.31 (m, 4H), 2.21 (t, J=6.9 Hz, 2H), 1.90 (m, 2H); ESI-MS (m/z, %): 369 (M+1); ESI-HRMS calculated for C20H25N4OS (MH+): 369.1743, Observed: 369.1754.

Provenance & Evidence