HCID 59004626, compound → HCID 178511911, compound

Participants

Reaction Steps

A solution of compound 76 (120 mg, 0.53 mmol) in EtOH (5 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (183 mg, 0.64 mmol) and stirred overnight at room temperature. Argon was bubbled through the mixture for 20 minutes then the suspension was diluted with CH2Cl2 (50 mL) and treated with saturated sodium bicarbonate (20 mL). The organic layer was separated and the aqueous layer was extracted with an additional CH2Cl2 (50 mL). The combined organic layers were dried over sodium sulfate and concentrated to give a yellow solid which was subjected to flash chromatography on silica gel (MeOH:CH2Cl2, 5:95 to 2M NH3 in MeOH:CH2Cl2, 5:95) to give compound 77 (86 mg, 48.9%) as a yellow solid. HPLC analysis indicated that the product is >99% pure. 1H NMR (DMSO-d6) δ 8.06 (d, J=2.5 Hz, 1H), 7.72 (d, J=3.4 Hz, 1H), 7.60-7.50 (m, 2H), 7.42 (d, J=3.0 Hz, 1H), 7.11-7.06 (m, 2H), 6.71 (d, J=8.9 Hz, 1H), 6.61 (d, J=8.8 Hz, 1H), 6.53 (d, J=3.0, 1H), 6.30 (brs, 2H), 6.16 (brs, 2H); ESI-MS (m/z, %): 334 (M+1, 100%); ESI-HRMS calculated for C18H16N5S (MH+): 334.1120, observed: 334.1135.

Provenance & Evidence