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A kind of synthetic method of ivabradine hydrochloride key intermediate

A technology of ivabradine hydrochloride and synthesis method, which is applied in chemical instruments and methods, carboxylate preparation, carboxylate preparation and other directions, can solve problems such as high price, achieve low risk, friendly reaction environment, and reaction conditions easy effect

Active Publication Date: 2022-08-02
株洲壹诺生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that compound 9 is used as the starting material, which is expensive

Method used

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  • A kind of synthetic method of ivabradine hydrochloride key intermediate
  • A kind of synthetic method of ivabradine hydrochloride key intermediate
  • A kind of synthetic method of ivabradine hydrochloride key intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] According to the reaction route of reaction formula (1)-(7), the first step: the reaction formula of reaction formula (1) is as follows:

[0047]

[0048] The method for preparing compound 2 in reaction formula (1) is as follows: take compound 1 (veratroaldehyde), malonic acid, and catalyst 1 into a reaction flask, add the reaction solvent of reaction formula (1), and after shaking to dissolve, set the reaction Temperature and reaction time, heating and refluxing for water separation reaction, after the reaction is completed, it is lowered to room temperature and water is added to stir, filter, wash with water, and dry to obtain compound 2. The specific reaction parameters are shown in the following table:

[0049]

[0050] Compound 2 1 H-NMR data: 1 H-NMR (400MHz, CDCl 3 ):δ: 3.98 (s, 3H), 3.99 (s, 3H), 7.46 (d, 1H), 7.70 (d, 1H), 7.90 (d, 1H), 8.32 (s, 1H).

[0051] Mass spectral data of compound 2: ESI+[M+H] + = 253.1

[0052] The second step: the reactio...

Embodiment 2

[0089] According to the synthesis method of Example 1, the difference is that the specific reaction parameters are changed.

[0090] The reaction parameters of reaction formula (1) are as follows:

[0091]

[0092] Compound 2 1 H-NMR data: 1 H-NMR (400MHz, CDCl 3 ):δ: 3.99 (s, 3H), 3.99 (s, 3H), 7.45 (d, 1H), 7.70 (d, 1H), 7.90 (d, 1H), 8.32 (s, 1H).

[0093] Mass spectral data of compound 2: ESI+[M+H] + =253.1

[0094] The reaction parameters of Equation (2) and Equation (3) are as follows:

[0095]

[0096] Compound 2 1 H-NMR data: 1 H-NMR (400MHz, CDCl 3 ):δ: 3.99 (s, 3H), 3.99 (s, 3H), 7.46 (d, 1H), 7.70 (d, 1H), 7.91 (d, 1H), 8.32 (s, 1H).

[0097] Mass spectral data of compound 4: ESI+[M+H] + =211.1

[0098] The reaction parameters of reaction formula (4) are as follows:

[0099]

[0100] Compound 5 1 H-NMR data: 1 H-NMR (400MHz, CDCl 3 ): δ: 7.02 (s, 1H), 6.78 (s, 1H), 3.85 (s, 6H), 3.01 (t, 2H), 2.69 (t, 2H)

[0101] Mass spectral data of compo...

Embodiment 3

[0115] According to the synthesis method of Example 1, the difference is that the specific reaction parameters are changed.

[0116] The reaction parameters of reaction formula (1) are as follows:

[0117]

[0118] Compound 2 1 H-NMR data: 1 H-NMR (400MHz, CDCl 3 ):δ: 3.98 (s, 3H), 3.99 (s, 3H), 7.44 (d, 1H), 7.70 (d, 1H), 7.91 (d, 1H), 8.32 (s, 1H).

[0119] Mass spectral data of compound 2: ESI+[M+H] + =253.1

[0120] The reaction parameters of Equation (2) and Equation (3) are as follows:

[0121]

[0122] Compound 2 1 H-NMR data: 1 H-NMR (400MHz, CDCl 3 ):δ: 3.98 (s, 3H), 3.99 (s, 3H), 7.45 (d, 1H), 7.71 (d, 1H), 7.91 (d, 1H), 8.32 (s, 1H).

[0123] Mass spectral data of compound 4: ESI+[M+H] + =211.1

[0124] The reaction parameters of reaction formula (4) are as follows:

[0125]

[0126] Compound 5 1 H-NMR data: 1 H-NMR (400MHz, CDCl 3 ): δ: 7.01 (s, 1H), 6.78 (s, 1H), 3.85 (s, 6H), 3.00 (t, 2H), 2.68 (t, 2H)

[0127] Mass spectral data of compo...

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Abstract

The present invention relates to the technical field of pharmaceutical synthesis, in particular to a method for synthesizing a key intermediate of ivabradine hydrochloride. The raw materials used in the synthesis method are cheap, the reaction conditions are not harsh, and the product yield is high, which is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical synthesis, in particular to a method for synthesizing a key intermediate of ivabradine hydrochloride. Background technique [0002] Ivabradine hydrochloride, chemical name: 7,8-dimethoxy-3-(3-[[(1S)(4,5-dimethoxybenzocyclobutan-1-yl )methyl]-methylamino]propyl)-1,3,4,5-tetrahydro-2hydro-benzazepine-2-one hydrochloride, the first sinoatrial node If current selective specific Sex inhibitors, whose simple action of slowing down heart rate has been a stable angina pectoris drug for the past 20 years, can significantly improve the quality of life of patients with heart failure. [0003] The synthetic route of ivabradine hydrochloride, in Chinese Journal of Medicinal Chemistry 20 (2), 106-109; 2010, reported the following improved method: [0004] [0005] Among them, the reaction conditions of the fifth step reaction are extremely harsh, and it is necessary to use liquid ammonia as the reac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/09C07C62/34
CPCC07C51/09C07C67/08C07C51/363C07C51/38C07C51/36C07C51/353C07C2602/06C07C62/34C07C69/757C07C59/64
Inventor 于欢庆徐群杰谢子刚张树磊
Owner 株洲壹诺生物技术有限公司
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