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1.1-4 (1-4) Synthesis of Compound 7
The resulting compound 6 (0.59 g, 0.85 mmol) was dissolved in formic acid (9 ml), and the mixture was stirred at room temperature for 20 h. Then, formic acid was distilled away under reduced pressure. The resulting product was purified by column chromatography (AcOEt) to yield compound 7a (ICG-001) as a white solid (0.26 g, 0.48 mmol, 57%). [0099] The resulting product was identified using MS spectrum and 1H NMR spectrum (having identical values in a literature) (FIG. 1).
Multi-step reaction with 5 steps
1.1: diethylamine / dichloromethane / 2 h / 20 °C
2.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h
2.2: 14 h / 20 °C
3.1: diethylamine / dichloromethane / 1 h / 20 °C
4.1: dichloromethane / 12 h / 20 °C
5.1: formic acid / 20 h / 20 °C
Multi-step reaction with 4 steps
1.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h
1.2: 14 h / 20 °C
2.1: diethylamine / dichloromethane / 1 h / 20 °C
3.1: dichloromethane / 12 h / 20 °C
4.1: formic acid / 20 h / 20 °C
Multi-step reaction with 7 steps
1.1: 0.33 h / 100 °C
1.2: 16 h / 20 °C
2.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h
2.2: 16 h / 20 °C
3.1: diethylamine / dichloromethane / 2 h / 20 °C
4.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h
4.2: 14 h / 20 °C
5.1: diethylamine / dichloromethane / 1 h / 20 °C
6.1: dichloromethane / 12 h / 20 °C
7.1: formic acid / 20 h / 20 °C
Multi-step reaction with 6 steps
1.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h
1.2: 16 h / 20 °C
2.1: diethylamine / dichloromethane / 2 h / 20 °C
3.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h
3.2: 14 h / 20 °C
4.1: diethylamine / dichloromethane / 1 h / 20 °C
5.1: dichloromethane / 12 h / 20 °C
6.1: formic acid / 20 h / 20 °C