A class of fxa inhibitors containing bisamido and alkoxyphenyl structures and uses thereof
A technology of triphenylchloromethane and alkyl, applied in the field of medicine for the treatment of venous thrombosis diseases
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Embodiment 1
[0020] The synthesis of embodiment 1 compound I-1
[0021]
[0022] A. Synthesis of Compound III
[0023] Compound II (1.26g, 10mmol) and triethylamine (3.04g, 30mmol) were dissolved in 10mL of dry DMF, stirred under cooling in an ice-water bath, slowly added dropwise from triphenylchloromethane (TrCl; 3.07g, 11mmol) and 10 mL of dry DMF solution. After the addition was complete, the resulting reaction mixture was stirred at room temperature for 3 hours, and TLC showed that the reaction was complete. The reaction mixture was poured into 120 mL of ice water, CH 2 Cl 2 (50mL×3) was extracted, and the extract phases were combined, washed with brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain compound III, a white solid, ESI-MS, m / z=369 ([M+H] + ).
[0024] B. Synthesis of Compound V-1
[0...
Embodiment 2
[0030] The synthesis of embodiment 2 compound 1-2
[0031]
[0032] A. Synthesis of Compound III
[0033] Compound II (1.26g, 10mmol) and triethylamine (3.04g, 30mmol) were dissolved in 10mL of dry DMF, stirred under cooling in an ice-water bath, slowly added dropwise from triphenylchloromethane (TrCl; 3.07g, 11mmol) and 10 mL of dry DMF solution. After the addition was complete, the resulting reaction mixture was stirred at room temperature for 3 hours, and TLC showed that the reaction was complete. The reaction mixture was poured into 120 mL of ice water, CH 2 Cl 2 (50mL×3) was extracted, and the extract phases were combined, washed with brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain compound III, a white solid, ESI-MS, m / z=369 ([M+H] + ).
[0034] B. Synthesis of Compound V-1
[...
Embodiment 3
[0040] The synthesis of embodiment 3 reference compound D-1
[0041] Compound D-1 is also a compound designed by the inventors during the research process (unpublished as of the filing date).
[0042]
[0043] A. Synthesis of Compound III
[0044] Compound II (1.26g, 10mmol) and triethylamine (3.04g, 30mmol) were dissolved in 10mL of dry DMF, stirred under cooling in an ice-water bath, slowly added dropwise from triphenylchloromethane (TrCl; 3.07g, 11mmol) and 10 mL of dry DMF solution. After the addition was complete, the resulting reaction mixture was stirred at room temperature for 3 hours, and TLC showed that the reaction was complete. The reaction mixture was poured into 120 mL of ice water, CH 2 Cl 2 (50mL×3) was extracted, and the extract phases were combined, washed with brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the obtained residue was pu...
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