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Under ambient conditions, a solution of 3 (500 mg, 0.86 mmol) and sodium 1,1-dicyanoethene-2,2-dithiolate (480 mg, 2.57 mmol) in DMF (25 mL) was stirred at 55 C for 1 hour. Then 2-decyltetradecylamine (394 mg, 1.11 mmol) and 3,5-difluoroiodoaniline[2] (371 mg, 1.46 mmol) were added to the reaction mixture. The resulting purple black solution was stirred at 55 C for 12 hours, and water (200 mL) was added to quench the reaction. The product was extracted with CH2Cl2 (3 × 50 mL), and the combined organic solution was washed with water, brine, and dried over anhydrous MgSO4. After removing the solvent under reduced pressure, the crude product was purified by silica gel column chromatography with CH2Cl2 as eluent. Compound 1 was obtained as a purple red solid (yield: 10 %).
4-[2-[4-[[2-[[3-[[2,2-dimethyl-4-(methylcarbamothioyl)piperazin-1-yl]methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]-2,6-difluoro-phenyl]ethyl]benzoic acid[ No CAS ]
4-[2-[4-[[2-[[3-[[4-(2-carboxyethylcarbamoyl)-2,2-dimethylpiperazin-1-yl]methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]-2,6-difluoro-phenyl]ethyl]benzoic acid[ No CAS ]
4-[2-[2,6-difluoro-4-[[2-[[3-[(4-methoxycarbonyl-2,2-dimethylpiperazin-1-yl)methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]phenyl]ethyl]benzoic acid[ No CAS ]
4-[2-[4-[[2-[[3-[[2,2-dimethyl-4-(methylsulfamoyl)piperazin-1-yl]methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]-2,6-difluoro-phenyl]ethyl]benzoic acid[ No CAS ]
4-[2-[4-[[2-[[3-[(4-acetyl-2,2-dimethylpiperazin-1-yl)methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]-2,6-difluoro-phenyl]ethyl]benzoic acid[ No CAS ]
methyl 4-[2-[2,6-difluoro-4-[[2-[[3-[[4-(4-hydroxybutylcarbamoyl)-2,2-dimethylpiperazin-1-yl]methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]phenyl]ethyl]benzoate[ No CAS ]
tert-butyl 4-[[3-[[3-[[3,5-difluoro-4-[2-(4-methoxycarbonylphenyl)ethyl]phenyl]carbamoyl]-4,5,6,7-tetrahydrobenzothiophen-2-yl]carbamoyl]phenyl]methyl]-3,3-dimethylpiperazine-1-carboxylate[ No CAS ]
methyl 4-[2-[4-[[2-[[3-[(2,2-dimethylpiperazin-1-yl)methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]-2,6-difluorophenyl]ethyl]benzoate dihydrochloride[ No CAS ]
methyl 4-[2-[4-[[2-[[3-[[4-[bis(2-methoxyethyl)sulfanoyl]-2,2-dimethylpiperazin-1-yl]methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]-2,6-difluorophenyl]ethyl]benzoate[ No CAS ]
methyl 4-[2-[2,6-difluoro-4-[[2-[[3-[[4-(4-methoxy-4-oxobutyl)-2,2-dimethylpiperazine-1-yl]methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]phenyl]ethyl]benzoate[ No CAS ]
methyl 4-[2-[2,6-difluoro-4-[[2-[[3-[[4-(3-methoxypropyl)-2,2-dimethylpiperazin-1-yl]methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]phenyl]ethyl]benzoate[ No CAS ]
methyl 4-[2-[4-[[2-[[3-[[4-[2-(tert-butoxycarbonylamino)acetyl]-2,2-dimethylpiperazin-1-yl]methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]-2,6-difluorophenyl]ethyl]benzoate[ No CAS ]
methyl 4-[2-[2,6-difluoro-4-[[2-[[3-[[4-(4-methoxybutylcarbamoyl)-2,2-dimethylpiperazin-1-yl]methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]phenyl]ethyl]benzoate[ No CAS ]
4-[2-[4-[[2-[[3-[(4-tert-butoxycarbonyl-2,2-dimethylpiperazin-1-yl)methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]-2,6-difluorophenyl]ethyl]benzoic acid[ No CAS ]
tert-butyl 4-[[3-[[3-[[4-[2-(4-carbamoylphenyl)ethyl]-3,5-difluorophenyl]carbamoyl]-4,5,6,7-tetrahydrobenzothiophen-2-yl]carbamoyl]phenyl]methyl]-3,3-dimethylpiperazine-1-carboxylate[ No CAS ]
N-[4-[2-(4-carbamoylphenyl)ethyl]-3,5-difluorophenyl]-2-[[3-[(2,2-dimethylpiperazin-1-yl)methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide dihydrochloride[ No CAS ]
methyl 4-[2-[2,6-difluoro-4-[[2-[[3-[(2,2,4-trimethylpiperazin-1-yl)methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]phenyl]ethyl]benzoate[ No CAS ]
methyl 4-[2-[2,6-difluoro-4-[[2-[[3-[[4-[(3-methoxy-3-oxopropyl)carbamoyl]-2,2-dimethylpiperazin-1-yl]methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]phenyl]ethyl]benzoate[ No CAS ]
tert-butyl 3-[[3-[[3-[[3,5-difluoro-4-[2-(4-methoxycarbonylphenyl)ethyl]phenyl]carbamoyl]-4,5,6,7-tetrahydrobenzothiophen-2-yl]carbamoyl]phenyl]methyl]-3,8-diazabicyclo[3.2.1]octane-8-carboxylate[ No CAS ]
methyl 4-[2-[4-[[2-[[3-[(2,2-dimethylpiperazin-1-yl)methyl]benzoyl]amino]-4,5,6,7-tetrahydrobenzothiophene-3-carbonyl]amino]-2,6-difluorophenyl]ethyl]benzoate[ No CAS ]