Synthesis of Novel Thiophene-Derived Compound

Example 9

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Step 1:

Compound 3 (231 mg, 1 mmol), amine tert-butyl 2-amino-4-(thiophen-2 yl)phenylcarbamate (290 mg, 1 mmol), and EDCI (382 mg, 2 mmol) were combined in Py (5 mL). The reaction was stirred at rt overnight. The mixture was concentrated to get a residue, which was purified by silica gel to get compound 4 (302 mg, 60%) as yellow solid.

Step 2:

Compound 4 (252 mg, 0.5 mmol) and TFA (1 mL) were combined in DCM (2 mL). The reaction was stirred at rt for 1 h. The mixture was concentrated to get a compound 011 (161, 80%) as yellow solid. LCMS: m/z=404 (M+H)⁺. ¹H NMR (400 MHz, DMSO) δ 9.66 (s, 1H), 8.00 (m, 1H), 7.93 (s, 1H), 7.46 (s, 1H), 7.36 (m, 1H), 7.31 (m, 1H), 7.30 (m 2H), 7.06 (m, 1H), 6.81 (m, 1H), 5.14 (s, 2H). 3.68 (m, 2H), 3.62 (m, 2H), 1.17 (m, 1H), 0.48 (m, 2H), 0.36 (m, 2H)