HCID 59004643, compound → HCID 178480324, compound

Participants

Reaction Steps

compound 103 (65 mg, 0.283 mmol) is charged to a small, argon purged flask fitted with a magnetic stir bar. Anhydrous ethanol (7 mL) and thiophene-2-carboximidothioic acid methyl ester hydroiodide (121.2 mg, 0.425 mmol) are added to the flask and the reaction was stirred under argon at ambient temperature for 17 hours, at which time the solvent was evaporated and the residue was partitioned between H2O and ethyl acetate and 1M sodium hydroxide solution added to adjust pH to 9. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered, concentrated and the residue purified via chromatography on silica gel (MeOH:CH2Cl2, 1:9 then 2M NH3 in MeOH:CH2Cl2, 5:95 to 1:9) to yield compound 104 (30 mg, 31.3%) as a yellow solid. 1H NMR (DMSO-d6) δ 1.47-1.76 (m, 4H), 2.16 (q, 1H, J=8.5 Hz), 2.25 (s, 3H), 2.50-2.59 (m, 1H), 2.92-3.02 (m, 1H), 3.97 (dd, 1H, J=14.1, 7.1 Hz), 4.23 (dd, 1H, J=14.0, 4.8 Hz), 6.23 (brs, 2H), 6.31 (d, 1H, J=3.0 Hz), 6.69 (d, 1H, J=8.3 Hz), 6.98 (s, 1H), 7.08-7.11 (m, 1H), 7.31 (d, 1H, J=3.0 Hz), 7.39 (d, 1H, J=8.6 Hz), 7.58 (d, 1H, J=5.2 Hz), 7.71 (d, 1H, J=3.7 Hz); ESI-MS (m/z, %): 339 (MH+, 100%); ESI-HRMS calculated for C19H23N4S (MH+): 339.1637, observed: 339.1653.

Provenance & Evidence