A class of intermediates for the preparation of anticancer drugs
A compound and solvent technology, which is applied in the field of intermediates for the preparation of drugs, can solve problems such as technical difficulties in anti-tumor drugs
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[0032] In the preparation of compounds of the invention, it may be necessary to protect certain interfering functionalities (eg, primary or secondary amines) of intermediates. The requirements for such protecting groups vary depending on the nature of the particular functional group and the conditions of the preparation method. Suitable amino protecting groups include acetyl, trifluoroacetyl, tert-butoxycarbonyl (Boc), benzyloxycarbonyl (Cbz), 9-fluorenylmethyleneoxycarbonyl (Fmoc), and the like. Suitable hydroxy protecting groups include allyl, acetyl, silyl, benzyl, trityl, p-methoxybenzyl, and the like. Such protecting groups can be easily determined by those skilled in the art (for details, refer to Protective Groups in Organic Synthesis, John Wiley & Sons, New York, Third Edition, 1999).
[0033] The compounds of the present invention and the corresponding preparation methods are further explained and listed below through examples and preparations. It should be understo...
Embodiment 1
[0040]
[0041]Compound A (prepared according to WO2015059668 literature) weighed 3.34g in a round bottom flask, added 5mL ethylene glycol and 50mL dichloromethane, In(OTf) 3 Weigh 562mg into it, under the protection of nitrogen, stir at room temperature for 8h, TLC detects the reaction progress, after the reaction is completed, add 20mL of ethyl acetate, 20mL of water, continue to stir for 30min, separate the organic phase, and continue to use ethyl acetate for the water phase. Wash 3 times, combine the organic phases, dry overnight with anhydrous sodium sulfate, concentrate to obtain a semi-solid state substance, add tert-butyl methyl ether to the substance, continue stirring for 8 hours, and a solid precipitates, filter the solid, and wash 3 times with tert-butyl methyl ether, The compound 1 was obtained by air drying at 30°C, a total of 3.0 g, with a yield of 90.4%. 1 H NMR (600MHz, CDCl 3 ):δ7.08(s,1H),5.75(s,1H),5.04(s,1H),4.65(s,2H),4.21~4.17(m,2H),4.01~3.97(m,2H), ...
Embodiment 2
[0043]
[0044] Compound A (prepared according to WO2015059668 literature) weighed 3.34g in a round bottom flask, added 5mL ethylene glycol and 50mL dichloromethane, In(OTf) 3 Weigh 562mg into it, under the protection of nitrogen, stir at room temperature for 8h, TLC detects the reaction progress, after the reaction is completed, add 20mL of ethyl acetate, 20mL of water, continue to stir for 30min, separate the organic phase, and continue to use ethyl acetate for the water phase. Wash 3 times, combine the organic phases, dry overnight with anhydrous sodium sulfate, concentrate to obtain a semi-solid state substance, add tert-butyl methyl ether to the substance, continue stirring for 8 hours, and a solid precipitates, filter the solid, and wash 3 times with tert-butyl methyl ether, Compound 2 was obtained by blast drying at 30°C, a total of 3.2 g, with a yield of 92.5%. 1 H NMR (600MHz, CDCl 3 ):δ7.07(s,1H),5.53(s,1H),5.14(s,1H),4.75(s,2H),4.24~4.20(m,2H),3.98~3.92(m,2H), ...
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