HCID 59004663, compound → HCID 178480247, compound

Participants

Reaction Steps

A solution of compound 61 (235 mg, 0.91 mmol) in EtOH (10 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (520 mg, 1.83 mmol) and stirred overnight at room temperature. Argon was bubbled through the mixture for 20 minutes then it was concentrated to give brownish oil. This residue was partitioned between CH2Cl2 (50 mL) with 10% MeOH and saturated sodium bicarbonate (20 mL). The aqueous layer was extracted with an additional CH2Cl2 (50 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to give a brown residue which was subjected to flash chromatography on silica gel (MeOH:CH2Cl2, 5:95 to 2M NH3 in MeOH:CH2Cl2, 1:9) to give compound 62 (154 mg, 46.1%) as a yellow solid. 1H NMR (DMSO-d6) δ 7.71 (d, J=2.9 Hz, 1H), 7.58 (d, J=5.1 Hz, 1H), 7.37-7.30 (m, 2H), 7.10-7.08 (m, 1H), 6.98 (s, 1H), 6.70 (dd, J=1.5, 6.9 Hz, 1H), 6.31 (d, J=3.0 Hz, 1H), 6.25 (brs, 2H), 4.15 (t, J=7.5 Hz, 2H), 2.79-2.75 (m, 1H), 2.19 (s, 3H), 2.05-1.15 (m, 10H); ESI-MS (m/z, %): 367 (M+1,50), 184 (M+2, 100); ESI-HRMS calculated for C21H27N4S (MH+): 367.1966, observed: 367.1937.

Provenance & Evidence