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A new preparation method of anegliptin intermediate 1,2-diamino-2-methylpropane

A technology of methylpropane and diamino, which is applied in the field of anegliptin intermediate 1,2-diamino-2-methylpropane, which can solve the problems of high raw material prices, increased risk, difficulty and danger

Active Publication Date: 2017-10-31
LIAONING BENYUAN PHARMACY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Anegliptin was originally developed by Sanwa Pharmaceutical Co., Ltd. in Japan. There are mainly two methods for the preparation of the important intermediate 1,2-diamino-2-methylpropane. One is to use 2-amino-2-methylpropane Base-1-propanol and liquid ammonia are used as raw materials, Raney nickel is used as a catalyst, and it is prepared by a high-pressure hydrogenation reaction at 3KPa. The preparation process requires a high-pressure hydrogenation kettle and dangerous liquid ammonia for preparation, which adds a certain degree of difficulty and difficulty to the production. Danger
The second is to use 2-amino-2-cyanopropane as a starting material and use Raney nickel as a catalyst to carry out high-pressure hydrogenation reaction. The raw materials used in this synthesis route are expensive, and high-pressure hydrogenation equipment is also required, increasing the hazards in production

Method used

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  • A new preparation method of anegliptin intermediate 1,2-diamino-2-methylpropane

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Experimental program
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Effect test

Embodiment 1

[0008] In the reactor, add sodium hydroxide (153.7g, 3.84mol), water (1610ml) and cool down to 0-2°C, add bromine (192g, 1.2mol) at this temperature, and stir at this temperature for 30 minutes , add 3-amino-3-methylbutanamide (116.2g, 1mol), keep the same temperature and stir for 2 hours, then slowly raise the temperature to room temperature, stir for 1 hour, then raise the temperature to 70-72°C for 2 hours, cool down To room temperature, slowly add sodium hydroxide (340g) at room temperature, then extract with ethyl acetate (1000ml×4), combine the extracts, dehydrate with 30g of anhydrous sodium sulfate, filter, concentrate to remove ethyl acetate, and the remaining liquid Fractions at 113-115°C were collected to obtain 78.5 g of colorless 1,2-diamino-2-methylpropane with a purity of 98% and a yield of 89%.

Embodiment 2

[0010] In the reactor, add sodium hydroxide (120g, 3mol), water (1610ml) and cool down to 0-2°C, add bromine (153.6g, 0.96mol) at this temperature, and stir at this temperature for 30 minutes. Add 3-amino-3-methylbutanamide (116.2g, 1mol), keep the same temperature and stir for 2 hours, then slowly raise the temperature to room temperature, stir for 1 hour, then raise the temperature to 70-72°C for 2 hours, cool down to Keep at room temperature and slowly add sodium hydroxide (340g), then extract with ethyl acetate (1000ml×4), combine the extracts, dehydrate with 30g of anhydrous sodium sulfate, filter, concentrate to remove ethyl acetate, and collect the remaining liquid The fraction at 113-115°C yielded 67.9 g of colorless 1,2-diamino-2-methylpropane with a purity of 98% and a yield of 77%.

Embodiment 3

[0012] In the reactor, add sodium hydroxide (153.7g, 3.84mol), water (1610ml) and cool down to 5-10°C, add bromine (160g, 1.0mol) at this temperature, and stir at this temperature for 30 minutes , add 3-amino-3-methylbutanamide (116.2g, 1mol), keep the same temperature and stir for 2 hours, then slowly raise the temperature to room temperature, stir for 1 hour, then raise the temperature to 70-72°C for 2 hours, cool down To room temperature, slowly add sodium hydroxide (340g) at room temperature, then extract with ethyl acetate (1000ml×4), combine the extracts, dehydrate with 30g of anhydrous sodium sulfate, filter, concentrate to remove ethyl acetate, and the remaining liquid Fractions at 113-115°C were collected to obtain 48.5 g of colorless 1,2-diamino-2-methylpropane with a purity of 97.6% and a yield of 55%.

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Abstract

The invention relates to a preparation method of an anagliptin intermediate 1,2-diamido-2-methylpropane (namely, a compound 1). Anagliptin is a DPP-IV inhibitor developed by the Sanwa Kagaku Kenkyusho Co, Ltd in Japan, and is mainly used for treating type-II diabetes mellitus; the compound 1 is an important intermediate for anagliptin synthesis. A structure of the compound 1 is represented in the specification.

Description

technical field [0001] The invention relates to a new preparation method of anegliptin intermediate 1,2-diamino-2-methylpropane. Background technique [0002] Anegliptin was originally developed by Sanwa Pharmaceutical Co., Ltd. in Japan. There are mainly two methods for the preparation of the important intermediate 1,2-diamino-2-methylpropane. One is to use 2-amino-2-methylpropane Base-1-propanol and liquid ammonia are used as raw materials, Raney nickel is used as a catalyst, and it is prepared by a high-pressure hydrogenation reaction at 3KPa. The preparation process requires a high-pressure hydrogenation kettle and dangerous liquid ammonia for preparation, which adds a certain degree of difficulty and difficulty to the production. Danger. The second is to use 2-amino-2-cyanopropane as a starting material and use Raney nickel as a catalyst to carry out high-pressure hydrogenation reaction. The raw materials used in this synthesis route are expensive, and high-pressure hy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/58C07C211/09
CPCC07C209/58C07C211/09
Inventor 陈家骏李昕昊王艳胡忠涛田雪郑益兵
Owner LIAONING BENYUAN PHARMACY CO LTD
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