Reversible fluorescent compound targeting tyrosine kinase recognition and its preparation method and application
A compound and composition technology, applied in the field of reversible fluorescent compounds, can solve the problems that molecular typing cannot be widely carried out, high detection cost, complicated operation, etc., and achieve the effect of strong practicability, good simplicity, and simple synthesis
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preparation Embodiment 1
[0051]
[0052] The synthetic route is the same as that of Chinese patent 201510418869.2 (application number). Add 2,4-dimethyl-pyrrole (2.2eq.) into the round bottom flask, dissolve in anhydrous dichloromethane, nitrogen protection, ice bath, drop 4-bromobutyryl chloride (1.0eq. .), heated to reflux for 8 hours after the dropwise addition, spin-dried dichloromethane, added toluene and dichloromethane (volume ratio of toluene to dichloromethane=19:1), ice bathed, added triethylamine (7.0eq.) , drop boron trifluoride-diethyl ether complex (7.0eq.) into the constant pressure low liquid funnel, after the addition is complete, remove the ice bath, react at room temperature for 10-20min, heat the reaction at 50°C for 3h, cool the reaction solution, pour Quenched in ice water, extracted with dichloromethane, dried over sodium sulfate, spin-dried the solvent, and purified by column to obtain product 3a, a reddish-brown solid, with a yield of 30%. 1 H NMR (400MHz, CDCl 3 )δ6.06(s...
preparation Embodiment 2
[0054]
[0055] Add 2,4-dimethyl-3-ethyl-pyrrole (2.2eq.) into the round bottom flask, dissolve in anhydrous dichloromethane, protect with nitrogen, ice bath, drop 4-bromo Butyryl chloride (1.0eq.), heated under reflux for 8h after the dropwise addition, spin-dried dichloromethane, added toluene and dichloromethane (volume ratio of toluene to dichloromethane=19:1), ice-bathed, added triethylamine (7.0eq.), drop boron trifluoride-diethyl ether complex (7.0eq.) into the constant pressure low liquid funnel, after the addition is completed, remove the ice bath, react at room temperature for 10-20min, heat at 50°C for 3h, The reaction solution was cooled, quenched by pouring into ice water, extracted with dichloromethane, dried over sodium sulfate, spin-dried to dry the solvent, and purified by column to obtain product 3b, a reddish-brown solid, with a yield of 30%. 1 HNMR (400MHz, CDCl 3 )δ4.38(s,1H),3.49(t,J=5.9Hz,2H),3.05–2.96(m,2H),2.43(t,J=6.5Hz,2H),2.23(q,J=6.8 Hz,4H),2....
preparation Embodiment 3
[0057]
[0058] The synthetic route is the same as that of Chinese patent 201510418869.2 (application number). Add the product (1.0eq.) obtained in Example 1 into the round bottom flask, dissolve in anhydrous dichloromethane and anhydrous dimethyl sulfoxide (DCM to DMSO volume ratio=4:1), nitrogen protection, ice bath, add Anhydrous triethylamine (5.0eq.), add sulfur trioxide-pyridine complex (3.0eq.), withdraw from the ice bath, react at room temperature for 30-60min, add water to quench the reaction, extract with dichloromethane, dry over sodium sulfate, The solvent was spin-dried, and the column was purified to obtain product 4a, a reddish-brown solid, with a yield of 37%. 1 H NMR (400MHz, CDCl 3 )δ9.91(s,1H),6.08(s,2H),3.33–3.24(m,2H),2.85–2.77(m,2H),2.54(s,6H),2.37(s,6H).
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