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Synthesis method of anti-tumor drug ribociclib

An anti-tumor drug, ribociclib technology, applied in the field of synthesis of anti-tumor drug ribociclib, can solve problems such as high cost and complicated steps, and achieve the effects of reducing production costs, shortening reaction steps, and simplifying experimental operations

Inactive Publication Date: 2019-11-05
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0020] The technical problem to be solved by the present invention is to provide a synthetic method of the antineoplastic drug Ribociclib, to overcome the defects of using transition metal palladium in the synthesis of Ribociclib in the prior art, complex steps and high cost

Method used

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  • Synthesis method of anti-tumor drug ribociclib
  • Synthesis method of anti-tumor drug ribociclib
  • Synthesis method of anti-tumor drug ribociclib

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Synthesis of N,N-Dimethyl-2,3-dibromopropionamide

[0062] Dissolve N,N-dimethylacrylamide (30.0g, 0.30mol) in 200ml of toluene, add bromine (50.4g, 0.30mol) dropwise at room temperature, drop it over in 30 minutes, continue to stir at room temperature for 2h, and the reaction is complete The latter toluene layer was washed with water (100 mL×2), dried over anhydrous sodium sulfate, and the toluene was evaporated under reduced pressure to obtain 73.5 g of white solid, yield: 95%.

Embodiment 2

[0064] Synthesis of N,N-Dimethyl-2,3-dibromopropionamide

[0065] Dissolve N,N-dimethylacrylamide (45.0g, 0.45mol) in 250ml of chloroform, add bromine (108.0g, 0.68mol) dropwise at room temperature, drop it over in 30 minutes, continue to stir at room temperature for 2h, and the reaction is complete The latter toluene layer was washed with water (100 mL×2), dried over anhydrous sodium sulfate, and the chloroform was evaporated under reduced pressure to obtain 106.0 g of white solid, yield: 92%.

Embodiment 3

[0067] Synthesis of N,N-Dimethylpropynamide

[0068]Dissolve the N,N-dimethyl-2,3-dibromopropionamide (40.0 g, 0.16 mol) prepared in Example 1 in 200 mL of tetrahydrofuran, cool in an ice bath to 0°C, and add potassium tert-butoxide in batches (18.0g, 0.16mol), add in 30 minutes, rise to room temperature and continue to stir the reaction for 2h, after the reaction is complete, distill off the tetrahydrofuran under reduced pressure, add 100ml of dichloromethane and 100ml of water, stir for 5min, separate the organic layer, Dry over sodium sulfate, evaporate dichloromethane under reduced pressure to obtain 10.6 g of white solid, yield: 68%, mp: 67-70°C.

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Abstract

The invention relates to a synthesis method of an anti-tumor drug ribociclib. The method mainly comprises the steps of carrying out a reaction between 4-(6-amino-3-pyridyl)-1-piperazinyl tert-butyl formate and 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-formamide under the effect of a catalyst, conducting extraction, removing a solvent through evaporation, conducting recrystallization, and carrying out a stirring reaction on obtained 4-[6-[[7-cyclopentyl-6-[(dimethyl)carbonyl]-7H-pyrrolo[2,3-d]pyrimidine-2-yl]-3-pyridyl]-1-piperazinyl tert-butyl formate in a hydrochloricacid solution to prepare the ribociclib. The preparing method is easy to operate and high in yield, a reaction route is short, few three wastes are generated, and industrial production is facilitated.

Description

technical field [0001] The invention belongs to the field of synthesis of antineoplastic drugs, in particular to a synthesis method of antineoplastic drug Ribociclib. Background technique [0002] Ribociclib (Ribociclib, I), chemical name: 7-cyclopentyl-N,N-dimethyl-2-[[5-(1-piperazine)-2-(pyridyl)amino]- 7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (7-cyclopentyl-N,N-dimethyl-2-[[5-(1-piperazinyl)-2-pyridinyl]amino]-7H-Pyrrolo [2,3-d]pyrimidine-6-carboxamide), molecular formula: C 23 h 30 N 8 O, CAS registry number: 1211441-98-3. This product is a new class of targeted small molecule drugs, which can selectively inhibit the activity of cyclin-dependent kinase 4 / 6 (CDK4 / 6), reduce the proliferation of breast cancer cell lines and play an anti-tumor effect. Clinical studies have confirmed that ribociclib combined with letrozole can prolong the progression-free survival of patients compared with letrozole alone. Therefore, the drug was approved by the FDA as a breakthrough ...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 赵圣印王文康祝家楠王乾坤
Owner DONGHUA UNIV
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