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Synthesis method of (3-cyclopropylpyridin-2-yl) methylamine hydrochloride

A technology of methylamine hydrochloride and cyclopropylpyridine, which is applied in the field of organic chemical intermediate synthesis, can solve problems such as no compound synthesis method reported in the literature, and achieve the effects of easy control, simple experimental operation and reasonable design.

Inactive Publication Date: 2020-06-16
阿里生物新材料(常州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Mainly solve the technical problem that there is no literature report on the synthesis method of this compound

Method used

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  • Synthesis method of (3-cyclopropylpyridin-2-yl) methylamine hydrochloride
  • Synthesis method of (3-cyclopropylpyridin-2-yl) methylamine hydrochloride
  • Synthesis method of (3-cyclopropylpyridin-2-yl) methylamine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Synthesis of Compound C

[0030] 3-Bromopyridine (23.7g, 150mmol, 1eq.) was dissolved in 350ml of dichloromethane, under an ice-salt bath, m-chloroperbenzoic acid (58g, 225mmol, 1.5eq.) with a mass fraction of 67% was added in batches . After the addition was complete, the reaction was carried out at 20° C. for 3 hours.

[0031] After the reaction was completed, 140 ml of saturated aqueous sodium bicarbonate solution was added under ice-cooling, and stirred for half an hour. Extracted with a mixture of dichloromethane and methanol (volume ratio 8:1), the obtained organic phase was dried, concentrated, and then purified by column chromatography to obtain 24.3g of light red oil 3-bromopyridine-N-oxide, Yield 93%.

[0032] 3-Bromopyridine-N-oxide (24.3g, 139.5mmol, 1eq.) was dissolved in 360ml of acetonitrile, under the protection of nitrogen, trimethylsilyl cyanide (41.5g, 418.5mmol, 3eq.), three Ethylamine (28.2g, 279mmol, 2eq.) was reacted at 75°C for 15 hours. ...

Embodiment 2

[0048] (1) Synthesis of Compound C

[0049]3-Bromopyridine (28.4g, 180mmol, 1eq.) was dissolved in 420ml of dichloromethane, under ice-salt bath, m-chloroperoxybenzoic acid (69.5g, 270mmol, 1.5eq. ). After the addition was complete, the reaction was carried out at 20° C. for 3 hours.

[0050] After the reaction was completed, 170 ml of saturated aqueous sodium bicarbonate solution was added under ice-cooling, and stirred for half an hour. Extracted with a mixture of dichloromethane and methanol (volume ratio 8:1), the obtained organic phase was dried, concentrated, and then purified by column chromatography to obtain 29.1g of light red oil 3-bromopyridine-N-oxide, Yield 93%.

[0051] 3-Bromopyridine-N-oxide (29.1g, 167.4mmol, 1eq.) was dissolved in 430ml of acetonitrile, under the protection of nitrogen, trimethylsilyl cyanide (49.8g, 502.2mmol, 3eq.), three Ethylamine (33.9g, 334.8mmol, 2eq.) was reacted at 75°C for 15 hours.

[0052] After the reaction was finished, aft...

Embodiment 3

[0067] (1) Synthesis of Compound C

[0068] 3-Bromopyridine (19g, 120mmol, 1eq.) was dissolved in 280ml of dichloromethane, under ice-salt bath, m-chloroperoxybenzoic acid (46.4g, 180mmol, 1.5eq.) was added in batches with a mass fraction of 67% . After the addition was complete, the reaction was carried out at 20° C. for 3 hours.

[0069] After the reaction was completed, 110 ml of saturated aqueous sodium bicarbonate solution was added under ice-cooling, and stirred for half an hour. Extracted with a mixture of dichloromethane and methanol (volume ratio 8:1), the obtained organic phase was dried, concentrated, and then purified by column chromatography to obtain 19.2g of light red oily 3-bromopyridine-N-oxide, Yield 92%.

[0070] 3-Bromopyridine-N-oxide (19.2g, 110.4mmol, 1eq.) was dissolved in 280ml of acetonitrile, under the protection of nitrogen, trimethylsilyl cyanide (32.9g, 331.2mmol, 3eq.), three Ethylamine (22.3g, 220.8mmol, 2eq.) was reacted at 75°C for 15 hour...

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Abstract

The invention provides a synthesis method of (3-cyclopropylpyridin-2-yl) methylamine hydrochloride, and belongs to the technical field of synthesis of organic chemical intermediates. The preparation method comprises the following steps: reacting 3-bromo-2-cyanopyridine with cyclopropylboronic acid, a phosphine ligand, an alkali and a catalyst under the protection of nitrogen, then reacting with hydrogen under the action of the catalyst, reacting with di-tert-butyl dicarbonate and alkali, and finally reacting with an organic solvent solution of hydrogen chloride to obtain a target product (3-cyclopropylpyridin-2-yl) methylamine hydrochloride. The 3-bromo-2-cyanopyridine is prepared by taking 3-bromopyridine as a raw material and carrying out nitrogen oxidation and cyanation. The method is reasonable in process design, simple in experimental operation and easy to control.

Description

technical field [0001] The invention relates to the technical field of synthesis of organic chemical intermediates, in particular to a synthesis method of (3-cyclopropylpyridin-2-yl)methylamine hydrochloride. Background technique [0002] Heterocyclic compounds, especially pyridine heterocyclic compounds, are an important class of compounds in medicinal chemistry. As an important fine chemical raw material, their derivatives mainly include aminopyridine, halogenated pyridine, cyanopyridine, etc., which are mainly used in new Pesticides, pharmaceuticals and other fields. [0003] Because the chemical structure of cyclopropyl is different from that of straight-chain aliphatic hydrocarbons and other polycyclic aliphatic rings, it is often used in the design of drug molecules, which can enhance drug efficacy, metabolic stability, affinity for receptors, etc. Therefore, cyclopropyl and methylamino groups are introduced on the pyridine ring to improve the biological activity of p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/38
CPCC07D213/38
Inventor 史建云刘超戴红升顾云龙江云青
Owner 阿里生物新材料(常州)有限公司
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