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Process for preparing 2-alkoxy-4-amino-5-methyl-pyridines and/or 2-alkoxy-4-alkylamino-5-methyl-pyridines

A technology of alkyl and cycloalkyl, applied in the field of compounds produced by it, can solve the problem of no 2-alkoxy-4-amino-5-picoline, etc.

Pending Publication Date: 2021-08-10
SALTIGO GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, no known from the literature for the preparation of such 2-alkoxy-4-amino-5-picoline and / or 2-alkoxy-4-alkylamino-5-picoline method

Method used

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  • Process for preparing 2-alkoxy-4-amino-5-methyl-pyridines and/or 2-alkoxy-4-alkylamino-5-methyl-pyridines
  • Process for preparing 2-alkoxy-4-amino-5-methyl-pyridines and/or 2-alkoxy-4-alkylamino-5-methyl-pyridines
  • Process for preparing 2-alkoxy-4-amino-5-methyl-pyridines and/or 2-alkoxy-4-alkylamino-5-methyl-pyridines

Examples

Experimental program
Comparison scheme
Effect test

example

[0108] Example 1a: Preparation of 4-amino-2-benzyloxy-5-picoline / 4-benzylamino-2-benzyloxy-5-picoline (the present invention)

[0109] A mixture of 60 g (0.55 mol) of benzyl alcohol and 40 g (0.22 mol) of a 30% methoxide sodium methoxide solution was heated to about 150° C. and the resulting methanol was distilled off. After reaching 150° C., a vacuum of 90 mbar was applied with continuous removal of distillate, and the mixture was stirred under these conditions for a further 1 hour. Subsequently, the vacuum was increased at 150° C. until distillation started. Distillation was continued under these conditions until the maximum temperature reached or exceeded 100°C.

[0110] At 150° C. and under standard pressure, a solution of 10 g (0.07 mol) of 4-amino-2-chloro-5-methylpyridine in 20 g (0.18 mol) of benzyl alcohol was then metered in over 2 hours. After metering, the reaction mixture was further stirred at 150° C. until conversion was complete.

[0111] After cooling to r...

example 3

[0146] Example 3: Preparation of 4-amino-2-propoxy-5-methylpyridine (the present invention)

[0147] In an autoclave, a mixture of 24 g (0.17 mol) of 4-amino-2-chloro-5-picoline, 120 g (2.0 mol) of n-propanol and 25.8 g (0.65 mol) of sodium hydroxide was heated to 145°C, and the mixture was stirred at these conditions for 24 hours.

[0148] After cooling to room temperature, 150 g of water were added to the reaction mixture, which was freed from alcohol by distillation at standard pressure to a minimum temperature of about 110°C. 90 g of toluene were added to the distillation bottoms and controlled at a temperature of about 50°C. At this temperature the aqueous phase separates out.

[0149] After adding another 90 g of water, the resulting mixture was adjusted to pH 8-9 with 30% aqueous hydrochloric acid. Subsequently, the toluene was separated off at standard pressure, and 12 g of isopropanol were added to the remaining suspension at about 70° C. After cooling to room t...

example 4

[0151] Example 4: Preparation of 4-amino-2-isopropoxy-5-picoline (present invention)

[0152] In an autoclave, a mixture of 24 g (0.17 mol) of 4-amino-2-chloro-5-picoline, 120 g (2.0 mol) of isopropanol and 25.8 g (0.65 mol) of sodium hydroxide was heated under spontaneous pressure to 145°C, and the mixture was stirred at these conditions for 24 hours.

[0153] After cooling to room temperature, 100 g of water were added to the reaction mixture, which was freed from alcohol by distillation at standard pressure to a minimum temperature of about 110°C. 90 g of toluene were added to the distillation bottoms and controlled at a temperature of about 50°C. At this temperature the aqueous phase separates out.

[0154] After adding another 90 g of water, the resulting mixture was adjusted to pH 8-9 with 30% aqueous hydrochloric acid. Subsequently, the toluene was separated off at standard pressure, and 12 g of isopropanol were added to the remaining suspension at about 70° C. Af...

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Abstract

The invention relates to a process for preparing 2-alkoxy-4-amino-5-methyl-pyridines of the formula (I) and / or 2-alkoxy-4-alkylamino-5-methyl-pyridines of the formula (II) from the corresponding 2-halogen-amino-pyridines and the corresponding alcohols in the presence of a base, and to the corresponding resulting compounds.

Description

technical field [0001] The present invention relates to a method for preparing 2-alkoxy-4-amino-5-methyl of formula (I) from the corresponding 2-haloaminopyridine and a suitable alcohol in the presence of a base or the corresponding alkoxide Pyridine and / or 2-alkoxy-4-alkylamino-5-picoline of formula (II) and to compounds produced therefrom. Background technique [0002] 2-Alkoxy-4-amino-5-picoline and 2-alkoxy-4-alkylamino-5-picoline are starting materials for the synthesis of pharmaceutical and agrochemical active ingredients. Such structural elements are found, for example, in WO2014 / 114578A2 in acetyl-CoA carboxylase inhibitors, which can be used in the treatment of, for example, diabetes or obesity. As active ingredients in WO 2014 / 124230 A2, such 2-alkoxy-4-amino-5-picolines of formula (I) are disclosed as starting points for the preparation of active ingredients from the group of ERK kinase inhibitors Materials, these kinase inhibitors can be used to treat cancer. ...

Claims

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Application Information

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IPC IPC(8): C07D213/73C07D213/74
CPCC07D213/73C07D213/74
Inventor 卡斯滕·冯·德姆·布鲁赫
Owner SALTIGO GMBH
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