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Synthesis method of rolapitant

A synthesis method and compound technology, applied in organic chemistry methods, organic chemistry and other directions, can solve the problems of low product yield, high cost and complexity, and achieve the effect of simple and easy synthesis method, good product quality and high yield.

Inactive Publication Date: 2017-11-24
SUZHOU XINEN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In the prior art, the synthesis process of rorapitant is often more complicated, the cost is higher, and there are also defects of low product yield and poor quality, which cannot be suitable for industrialized large-scale production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0029] Preparation of compound (3)

[0030] At room temperature, add 5.8 kg (10 mol) of compound (2) into a 50L reaction kettle, then add 20L toluene, add 1.18 kg (11 mol) of benzylamine, heat up to reflux, monitor the reaction by TLC, and concentrate under reduced pressure to obtain The crude product of compound (3) was recrystallized from ethyl acetate to obtain 6.46 kg (9.67 mol) of the refined product of compound (3), with a yield of 96.7%. HPLC detection purity: 99.2%.

[0031] 1 H NMR (400 MHz, CDCl 3 ) δ 7.76 (s, 1H), 7.72 – 7.54 (s, 2H), 7.41 –7.10 (m, 15H), 5.87 – 5.65 (m, 1H), 5.41 – 5.23 (m, 1H), 4.85 – 4.56 (m , 5H),4.06 (d, J = 12.5 Hz, 1H), 3.81 (d, J = 17.4 Hz, 1H), 3.60 (d, J = 12.3 Hz,1H), 2.70 – 2.41 (m, 1H), 2.39 – 2.15 (m, 2H), 1.34 (d, J = 5.7 Hz, 3H).

[0032] ESI+ [M+H] + =669.

[0033] Preparation of compound (5)

[0034] Under the protection of nitrogen, 5.34 kg (8.0 mol) of compound (3) was added to a 50L reactor at -20°C, and the catal...

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Abstract

The present invention provides a method for synthesizing the compound of formula (1) rorapitant. The compound of formula (2) is used as the starting material, and through the following series of reactions, the compound of formula (1) is finally obtained, that is, the rorapitant : Compared with the synthesis steps of rorapitant in the prior art and the complex synthesis process, the synthesis method of the present invention is simple and easy, has low cost, high yield, good product quality, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing rorapitant, which belongs to the technical field of drug synthesis. Background technique [0002] Rorapitant (common name: rolapitan, trade name Varubi), chemical name: (5S,8S)-8-{[(1R)-1-[3,5-bis(trifluoromethyl)phenyl] Ethoxy]methyl}}-8-phenyl-1,7-diazaspiro[4.5]decan-2-one monohydrochloride monohydrate, molecular formula: C 25 h 26 f 6 N 2 o 2 ·HCl·H 2 O. The molecular weight of the rorapitant complex: 554.95; CAS registration number: 552292-08-7; the structural formula is shown in formula 1: [0003] [0004] Formula 1 [0005] Rorapitant was developed by Tesaro. Approved in the United States on September 2, 2015, for the treatment of delayed-phase nausea and vomiting induced by initial and repeat chemotherapy in adult cancer patients. Rorapitant, a P / neurokinin-1 (NK-1) receptor antagonist, activates NK that plays a central role in nausea and vomiting induced by certain cancer chemoth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/10
CPCC07D471/10C07B2200/07
Inventor 王保安
Owner SUZHOU XINEN PHARMA
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