CN115745902A - Preparation method of N-triazine amide compound - Google Patents
Preparation method of N-triazine amide compound Download PDFInfo
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Abstract
The invention provides a preparation method of an N-triazine amide compound, and the preparation method is convenient to operate, easy to obtain raw materials and has a certain application value. The N-triazine amide compound provided by the invention shows certain biological activity of resisting liver cancer and breast cancer, and lays a foundation for screening and developing new drugs.
Description
(I) technical field
The invention relates to a preparation method of an N-triazine amide compound.
(II) background of the invention
Amide compounds are important organic synthetic units and also are the basic backbone for many drugs and natural products. The traditional amido bond is mainly prepared by condensation reaction of acyl chloride or carboxylic acid and amine, but the method has the defects of easy decomposition of used raw materials, difficult removal of byproducts, difficult control of reaction conditions, complicated post-treatment, poor yield and the like, and is limited to a certain extent in the use process. Triazine compounds have various biological activities of resisting cancer, resisting bacteria, resisting malaria, weeding and the like, and are one of hot spots of research of scientists in recent years, so that the development of a preparation method of the N-triazine amide compounds has certain practical application value.
Disclosure of the invention
The invention provides a preparation method of an N-triazine amide compound.
The invention adopts the following technical scheme:
the invention provides a preparation method of an N-triazine amide compound shown in a formula (I), which comprises the following steps:
mixing a triazine compound shown in a formula (II), a ketone compound shown in a formula (III), copper salt and halogen, adding into a solvent, stirring and reacting for 8-20 hours (preferably 8-13.5 hours and most preferably 13.5 hours) at 90-140 ℃ (preferably 120-140 ℃, most preferably 140 ℃), and carrying out post-treatment on the obtained reaction liquid to obtain an N-triazine amide compound shown in a formula (I); the amount ratio of the triazine compound shown in the formula (II), the ketone compound shown in the formula (III), the copper salt and the halogen is 1: 2.2-3.0: 0.2 to 0.5: 1.0-3.0 (preferably 1; the solvent is one or a mixed solvent of N, N-dimethylformamide, chlorobenzene, 1,2-dichlorobenzene and diethylene glycol dimethyl ether (preferably a mixed solvent of 1,2-dichlorobenzene and diethylene glycol dimethyl ether with the volume ratio of 2:1);
in the formulae (I), (II), (III), R 1 Or R 2 Each independently of the other is C1-C10 alkyl, or R 1 、R 2 And N between the two is combined to form a C4-C8 heterocyclic ring containing N or N, O; r is 3 Is phenyl or phenyl substituted by C1-C10 alkyl, C1-C10 alkoxy or halogen.
Further, R 1 、R 2 Each independently of the other is preferably methyl, or R 1 、R 2 And the combination of N between the two forms a tetrahydropyrrole ring, a piperidine ring or a morpholine ring.
Further, R 3 Is phenyl or phenyl substituted by methyl, methoxy, halogen or nitro.
Still further, the N-triazine amide compound represented by the formula (I) is one of the following:
preferably, the cupric salt is one or a mixture of more than two of cuprous chloride, cuprous bromide, cupric chloride and cupric acetate, and is preferably cupric chloride.
Preferably, the halogen in the reaction system is iodine.
Further, the volume of the solvent is 6 to 8mL/mmol, preferably 6mL/mmol, based on the amount of the triazine compound represented by formula (II).
The invention particularly provides a preparation method of an N-triazine amide compound shown in a formula (I), which comprises the following steps:
mixing a triazine compound shown in a formula (II), a ketone compound shown in a formula (III), copper salt and halogen, adding into a solvent, stirring and reacting at 140 ℃ for 13.5 hours, and carrying out post-treatment on the obtained reaction liquid to obtain an N-triazine amide compound shown in a formula (I); the amount ratio of the triazine compound shown in the formula (II), the ketone compound shown in the formula (III), the copper salt and the halogen is 1:2.2:0.4:1.5; the solvent is prepared from the following components in a volume ratio of 2: 11,2-dichlorobenzene and diethylene glycol dimethyl ether.
In the preparation method of the invention, the post-treatment comprises the following steps: adding a 10% sodium thiosulfate aqueous solution into the reaction solution, extracting with ethyl acetate, combining organic layers, drying with anhydrous sodium sulfate, concentrating, and mixing the organic layers in a volume ratio of 1:1, performing column chromatography separation by using a mixed solution of petroleum ether and ethyl acetate as an eluent, collecting an eluent containing a target compound, decompressing, distilling off the solvent and drying to obtain the N-triazine amide compound shown in the formula (I).
Further, the volume of the aqueous sodium thiosulfate solution is 60mL/mmol based on the amount of the triazine compound represented by the formula (II).
Compared with the prior art, the invention has the beneficial effects that:
the invention develops a preparation method of the N-triazine amide compound, and the process has the advantages of convenient operation, easily obtained raw materials and certain application value. The N-triazine amide compound provided by the invention shows certain biological activity of resisting liver cancer and breast cancer, and lays a foundation for screening and developing new drugs.
(IV) detailed description of the preferred embodiments
The invention will now be further illustrated by the following examples, without limiting the scope of the invention thereto.
The raw material triazine compound (II) used in the invention is prepared by reacting ester and biguanide under the action of sodium methoxide at room temperature; specific synthetic methods are described in literature (Bioorganic & Medicinal Chemistry Letters,19 (2009), 5644-5647); the purity of the N-triazine amide compound shown in the formula (I) obtained in the embodiment is more than 97%.
Example 1: preparation of Compound (I-1)
2-amino-4-dimethylamino-1,3,5-triazine (69.6mg, 0.5mmol), acetophenone (132.2mg, 1.10mmol), I 2 (190.4mg,0.75mmol),CuCl 2 ·2H 2 O (34.1mg, 0.20mmol), 1,2-dichlorobenzene (2 mL) and diethylene glycol dimethyl ether (1 mL) in a mixed solvent, and stirring the mixture in an oil bath at 140 ℃ for reaction for 13.5 hours, and stopping the reaction. After adding 30mL of a 10% aqueous solution of sodium thiosulfate, extraction with ethyl acetate (4 × 20 mL), combining the organic layers, drying over anhydrous sodium sulfate, filtration, concentration of the filtrate, column chromatography (petroleum ether: ethyl acetate =1, v), collection of the eluent containing the objective compound, distillation under reduced pressure, and drying, the objective compound (I-1) was obtained in 81mg with a yield of 67%.
1 H NMR(500MHz,CDCl 3 )δ8.85(br,1H),8.32(s,1H),7.88(dt,J＝7.5,1.0Hz,2H),7.57(tt,J＝7.5,1.0Hz,1H),7.48(t,J＝7.5Hz,2H),3.20(s,3H),3.17(s,3H).
Example 2:
adding CuCl 2 ·2H 2 O was changed to CuBr (28.6 mg, 0.2mmol), and the other operations were carried out in the same manner as described aboveExample 1, 10.1mg, yield 8.1%.
Example 3:
adding CuCl 2 ·2H 2 Changing O to Cu (OAc) 2 (41.6mg, 0.2mmol), the other operations were performed in the same manner as in example 1,9.0mg, resulting in a yield of 7.4%.
Example 4:
adding CuCl 2 ·2H 2 The operation was otherwise the same as in example 1, 15.0mg, except that O was changed to CuCl (19.8mg, 0.2mmol), and the yield was 12.3%.
Example 5:
the procedure of example 1 was otherwise the same as in example 1 except that the mixed solvent of 1,2-dichlorobenzene and diethylene glycol dimethyl ether was changed to chlorobenzene (3 mL), and the yield was 17.9 mg.
Example 6:
the same procedures as in example 1 were repeated except that the mixed solvent of 1,2-dichlorobenzene and diethylene glycol dimethyl ether was changed to DMF (3 mL), and the yield was 11.5 mg.
Example 7:
the procedure of example 1 was otherwise the same as in example 1 except that the mixed solvent of 1,2-dichlorobenzene and diethylene glycol dimethyl ether was changed to diethylene glycol dimethyl ether (3 mL), and the yield was 23 mg.
Example 8:
the mixed solvent of 1,2-dichlorobenzene and diethylene glycol dimethyl ether was changed to 1,2-dichlorobenzene (3 mL), and the other operations were the same as in example 1, 42.3mg, with a yield of 35%.
Example 9:
the procedure of example 1 was otherwise the same as in example 1 except that the mixed solvent of 1,2-dichlorobenzene and diethylene glycol dimethyl ether was changed to 1,2-dichlorobenzene (4 mL), and the yield was 36.3 mg.
Example 10:
the mixed solvent of 1,2-dichlorobenzene and diethylene glycol dimethyl ether was changed to 1,3,5-trichlorobenzene (4 mL), and the other operations were the same as in example 1 to obtain a trace amount of the target product.
Example 11:
the mixed solvent of 1,2-dichlorobenzene and diethylene glycol dimethyl ether was changed to dioxane (4 mL), and the other operations were the same as in example 1 to obtain a trace amount of the target product.
Example 12:
adding CuCl 2 ·2H 2 The amount of O used was increased to 42.6mg (0.25mmol), and the other operations were carried out in the same manner as in example 1, 78.9mg, giving a yield of 63.3%.
Example 13:
adding CuCl 2 ·2H 2 The amount of O used was reduced to 17.1mg and 0.1mmol, and the other operations were carried out in the same manner as in example 1 to 52mg, whereby the yield was 43%.
Example 14:
will I 2 The amount of (D) was reduced to 380.7mg,0.50mmol, and the other operations were carried out in the same manner as in example 1, 68.8mg, giving a yield of 55.4%.
Example 15:
will I 2 The amount of (1) was increased to 380.7mg,1.50mmol and the other operations were carried out in the same manner as in example 1 or 11.3mg with a yield of 9.3%.
Example 16:
the amount of acetophenone was increased to (180.2mg, 1.50mmol), and the other operations were carried out in the same manner as in example 1, 70.3mg, giving a yield of 58.7%.
Example 17:
the reaction time was shortened to 8 hours, and the other operations were carried out in the same manner as in example 1, 40.5mg, giving a yield of 34.1%.
Example 18:
the reaction time was extended to 20 hours, and the other operations were carried out in the same manner as in example 1, 16mg, giving a yield of 13.3%.
Example 19:
the reaction temperature was changed to 90 ℃ and the other operations were carried out in the same manner as in example 1,3.6mg, giving a yield of 3%.
Example 20: preparation of Compound (I-2)
The same operation as in example 1 was conducted except that acetophenone was replaced with p-fluoroacetophenone (147.6 mg,1.1 mmol), and the other same operation as in example 1 was conducted to obtain the objective compound (I-2) in 77.6mg with a yield of 61%.
1 H NMR(400MHz,CDCl 3 )δ8.80(br,1H),8.35(s,1H),7.96-7.87(m,2H),7.21-7.12(m,2H),3.20(s,3H),3.17(s,3H).
Example 21: preparation of Compound (I-3)
The same operation as in example 1 was conducted except that acetophenone was replaced by p-chloroacetophenone (170.1mg, 1.1mmol), and the other operations were conducted as in example 1 to obtain the objective compound (I-3) in 82.5mg in 62% yield.
1 H NMR(400MHz,CDCl 3 )δ8.78(br,1H),8.37(s,1H),7.85-7.81(m,2H),7.48-7.44(m,2H),3.21(s,3H),3.17(s,3H).
Example 22: preparation of Compound (I-4)
The same operation as in example 1 was carried out except that acetophenone was replaced with p-methylacetophenone (147.6 mg,1.1 mmol), and the same operation as in example 1 was carried out to obtain the objective compound (I-4) in a yield of 92.7mg (73.4%).
1 H NMR(400MHz,CDCl 3 )δ8.59(br,1H),8.38(s,1H),7.80(d,J＝8.4Hz,m,2H),7.28(d,J＝8.4Hz,2H),3.21(s,6H),3.20(s,6H),2.42(s,3H).
Example 23: preparation of Compound (I-5)
The same operation as in example 1 was carried out except for changing the acetophenone to m-chloroacetophenone (170.1mg, 1.1mmol) and the same operation as in example 1 was carried out to obtain the objective compound (I-5) in 80.0mg with a yield of 58%.
1 H NMR(400MHz,CDCl 3 )δ9.13(br,1H),8.40(s,1H),7.93(s,1H),7.80(d,J＝7.8Hz,1H),7.55(d,J＝7.8Hz,1H),7.42(t,J＝7.8Hz,1H),3.22(s,3H),3.19(s,3H).
Example 24: preparation of Compound (I-6)
The same procedures as in example 1 were repeated except for changing 2-amino-4-dimethylamino-1,3,5-triazine to 2-amino-4-piperidine-1,3,5-triazine (89.6 mg, 0.50mmol) and using example 1, the objective compound (I-6) was obtained in an amount of 105.8mg with a yield of 76%.
1 H NMR(400MHz,CDCl 3 )δ8.85(br,1H),8.49-8.18(m,1H),7.88(d,J＝7.8Hz,2H),7.57(t,J＝7.8Hz,1H),7.48(t,J＝7.8Hz,2H),3.93-3.63(m,4H),1.70-1.60(m,6H).
Example 25: preparation of Compound (I-7)
The same procedures as in example 1 were repeated except for changing 2-amino-4-dimethylamino-1,3,5-triazine to 2-amino-4-morpholine-1,3,5-triazine (90.6 mg, 0.50mmol) and using example 1, the objective compound (I-7) was obtained in an amount of 88.3mg with a yield of 60%.
1 H NMR(400MHz,CDCl 3 )δ8.76(br,1H),8.36-8.34(m,1H),7.90-7.87(m,2H),7.60-7.55(m,1H),7.53-7.45(m,2H),3.93-3.80(m,4H),3.78-3.70(m,4H)
Example 26: preparation of Compound (I-8)
The same operation as in example 1 was carried out except for changing acetophenone to o-fluoroacetophenone (179.6 mg,1.3 mmol) and the same operation as in example 1 was carried out to obtain the objective compound (I-8) in 67.7mg with a yield of 53%.
1 H NMR(400MHz,CDCl 3 )δ9.01(br,1H),8.45(s,1H),8.10-8.05(m,1H),7.57-7.51(m,1H),7.33-7.27(m,1H),7.20-7.15(m,1H),3.21(s,3H),3.14(s,3H).
Example 27: preparation of Compound (I-9)
The same operation as in example 1 was carried out, except that acetophenone was replaced with bromoacetophenone (218.9mg, 1.1mmol), and the same operation as in example 1 was carried out, to give the title compound (I-9) in a yield of 60% at 94.4 mg.
1 H NMR(400MHz,CDCl 3 )δ9.04(br,1H),8.34(s,1H),7.75(d,J＝8.6Hz,2H),7.61(d,J＝8.6Hz,2H),3.20(s,3H),3.13(s,3H).
Example 28: preparation of Compound (I-10)
The same operation as in example 1 was carried out except for replacing acetophenone by m-methylacetophenone (174.4 mg,1.3 mmol) and the same operation as in example 1 was carried out to obtain the objective compound (I-10) in 64.0mg, yield 51%.
1 H NMR(400MHz,CDCl 3 )δ8.79(br,1H),8.34-8.30(m,1H),7.70(s,1H),7.68-7.62(m,1H),7.39-7.34(m,2H),3.19(s,6H),2.42(s,3H).
Example 29: preparation of Compound (I-11)
The same operation as in example 1 was carried out, except that acetophenone was changed to p-nitroacetophenone (214.7mg, 1.3mmol) and the other operation as in example 1 was carried out, to give the objective compound (I-11) in 87.0mg, yield 61%.
1 H NMR(400MHz,DMSO)δ11.12(br,1H),8.43(s,1H),8.31(d,J＝8.5Hz,2H),8.05(d,J＝8.5Hz,2H),3.11(s,3H),2.98(s,3H).
Example 30: preparation of Compound (I-12)
The same operation as in example 1 was carried out except for replacing acetophenone by m-bromoacetophenone (258.8mg, 1.3mmol) and the same operation as in example 1 was carried out to obtain the objective compound (I-12) in 78.4mg with a yield of 51%.
1 H NMR(400MHz,CDCl 3 )δ8.82(br,1H),8.39(s,1H),8.08-8.01(m,1H),7.82-7.80(m,1H),7.71-7.68(m,1H),7.37(t,J＝7.9Hz,1H),3.21(s,3H),3.16(s,3H).
Example 31: preparation of Compound (I-13)
The same operation as in example 1 was carried out except for changing the acetophenone to m-methoxyacetophenone (225.3mg, 1.5 mmol) and the same operation as in example 1 was carried out to obtain the objective compound (I-13) in 76.1mg with a yield of 56%.
1 H NMR(400MHz,CDCl 3 )δ8.74(br,1H),8.35(s,1H),7.45-7.41(m,2H),7.38(t,J＝7.9Hz,1H),7.12-7.09(m,1H),3.86(s,3H),3.20(s,3H),3.19(s,3H).
Example 32: preparation of Compound (I-14)
The same procedures as in example 1 were repeated except for changing 2-amino-4-dimethylamino-1,3,5-triazine to 2-amino-4-pyrrolidine-1,3,5-triazine (82.6 mg, 0.50mmol) and acetophenone to p-fluoroacetophenone (179.6 mg, 1.3mmol) and changing the same procedures as in example 1 to obtain the objective compound (I-14) in 62.2mg with a yield of 44.5%.
1 H NMR(400MHz,CDCl 3 )δ8.85(br,1H),8.34(s,1H),7.93-7.88(m,2H),7.26-7.11(m,2H),3.60-3.52(m,4H),2.00-1.94(m,4H).
Example 33: in vitro anti-human liver cancer cell (HEPG 2) or human breast cancer cell (T47D) bioactivity test method: MTT method experimental procedure:
1) Preparation of samples: for soluble samples, each 1mg was dissolved in 20. Mu.L DMSO, 2. Mu.L was diluted with 1000. Mu.L of culture medium to a concentration of 100. Mu.g/mL and then diluted with culture medium to 60. Mu. Mol/L.
2) Culture of cells
2.1 Preparation of culture medium, each 1000mL of culture medium contains 80 ten thousand units of penicillin, 1.0g of streptomycin and 10% inactivated fetal bovine serum.
2.2 Culture of cells): inoculating the tumor cells into the culture medium, placing at 37 deg.C, 5% 2 Culturing in an incubator, and carrying out passage for 3-5 days.
3) Determination of the inhibition of tumor cell growth by samples
The cells were digested with EDTA-pancreatin digest and diluted to 1X 10 with medium 5 Perml, added to a 96-well cell culture plate at 100uL per well, 37 ℃,5% CO 2 Culturing in an incubator. 24h after inoculation, samples diluted with medium were added, 100. Mu.L per well, 3 wells per sample, and the resulting mixture was incubated at 37 ℃ and 5% CO 2 The culture in the incubator, after 72h, adds 5mg/mL MTT to the cell culture wells, 10. Mu.L per well, incubate at 37 ℃ for 4h, add DMSO, 150. Mu.L per well, shake with a shaker, completely solubilize the formazan, and color with a microplate reader at a wavelength of 570 nm. The inhibition rate of the sample on the tumor cells was calculated by using cells cultured in the medium containing no sample and the same concentration of DMSO as a control under the same conditions, and the results are shown in Table 1.
The inhibition effect of 10 samples of the compounds (I-2) to (I-11) on the growth of liver cancer cells or human breast cancer cells in vitro was determined by using human liver cancer cells (HEPG 2) or human breast cancer cells (T47D) as a model (the results are detailed in Table 1).
TABLE 1 inhibition rate (60. Mu. Mol/L) of each compound on human hepatoma cells (HEPG 2) or human breast cancer cells (T47D)
Claims (10)
1. A preparation method of an N-triazine amide compound shown in formula (I) is characterized by comprising the following steps:
mixing a triazine compound shown in a formula (II), a ketone compound shown in a formula (III), copper salt and halogen, adding into a solvent, stirring and reacting for 8-20 hours at 90-140 ℃, and carrying out aftertreatment on the obtained reaction liquid to obtain an N-triazine amide compound shown in a formula (I); the amount ratio of the triazine compound shown in the formula (II), the ketone compound shown in the formula (III), the copper salt and the halogen is 1: 2.2-3.0: 0.2 to 0.5:1.0 to 3.0; the solvent is one or a mixed solvent of N, N-dimethylformamide, chlorobenzene, 1,2-dichlorobenzene and diethylene glycol dimethyl ether;
in the formulae (I), (II), (III), R 1 Or R 2 Each independently of the other is C1-C10 alkyl, or R 1 、R 2 And N between the two is combined to form a C4-C8 heterocyclic ring containing N or N, O; r 3 Is phenyl or phenyl substituted by C1-C10 alkyl, C1-C10 alkoxy or halogen.
2. A process for the preparation of N-triazine amide compounds of formula (I) according to claim 1, which comprises: r 1 Or R 2 Each independently of the other is preferably methyl, or R 1 、R 2 And the combination of N between the two forms a tetrahydropyrrole ring, a piperidine ring or a morpholine ring; r 3 Is phenyl or phenyl substituted by methyl, methoxy, halogen or nitro.
3. A process for the preparation of N-triazine amides of formula (I) as claimed in claim 1 or 2, characterized in that: the N-triazine amide compound shown in the formula (I) is one of the following compounds:
4. a process for the preparation of N-triazine amide compounds of formula (I) according to claim 1, which comprises: the temperature of the stirring reaction is 120-140 ℃.
5. A process for the preparation of N-triazine amides of formula (I) as claimed in claim 1, characterized in that: the solvent is prepared from the following components in a volume ratio of 2: 11,2-dichlorobenzene and diethylene glycol dimethyl ether.
6. A process for the preparation of N-triazine amides of formula (I) as claimed in claim 1, characterized in that: the copper salt is one or a mixture of more than two of cuprous chloride, cuprous bromide, cupric chloride and cupric acetate.
7. A process for the preparation of N-triazine amides of formula (I) as claimed in claim 1, characterized in that: the halogen is iodine.
8. A process for the preparation of N-triazine amides of formula (I) as claimed in claim 1, characterized in that: the volume of the solvent is 6 to 8mL/mmol based on the amount of the triazine compound represented by formula (II).
9. A process for the preparation of N-triazine amides of formula (I) as claimed in claim 1, characterized in that: the post-treatment comprises the following steps: adding a 10% sodium thiosulfate aqueous solution into the reaction solution, extracting with ethyl acetate, combining organic layers, drying with anhydrous sodium sulfate, concentrating, and mixing the organic layers in a volume ratio of 1:1, performing column chromatography separation by using a mixed solution of petroleum ether and ethyl acetate as an eluent, collecting an eluent containing a target compound, decompressing, distilling off the solvent and drying to obtain the N-triazine amide compound shown in the formula (I).
10. The process for producing an N-triazine amide compound represented by the formula (I) as claimed in claim 9, which comprises: the volume of the aqueous sodium thiosulfate solution is 60mL/mmol based on the amount of the triazine compound represented by the formula (II).
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