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Processes for the preparation of benzamide derivatives, novel intermediates for the preparation of benzamides, and processes for the preparation of novel intermediates

A technology for methylamine and tertiary amine is applied in the fields of preparing benzamide derivatives, novel intermediates for preparing benzamide and preparing novel intermediates, and achieves the effect of reducing reaction time and simplifying reaction process

Active Publication Date: 2017-12-19
东亚ST 株式会社
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although 5-HT4 receptor agonists are widely available, few 5-HT4 receptor agonist compounds are currently used in the clinical stage

Method used

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  • Processes for the preparation of benzamide derivatives, novel intermediates for the preparation of benzamides, and processes for the preparation of novel intermediates
  • Processes for the preparation of benzamide derivatives, novel intermediates for the preparation of benzamides, and processes for the preparation of novel intermediates
  • Processes for the preparation of benzamide derivatives, novel intermediates for the preparation of benzamides, and processes for the preparation of novel intermediates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0151] [Example 1] Preparation of 1-(3-chloropropyl)-1H-1,2,3-triazole (formula 5)

[0152] The preparation of step 1.1-azido-3-chloropropane (formula 8)

[0153] Dimethylsulfoxide (126 L) was added to the reaction portion, and then 3-bromo-1-chloropropanol (14 kg) was added thereto at room temperature. A reaction solution was prepared by adding sodium azide (5.8 kg) thereto, washing the reaction part with dimethyl sulfoxide (14 L) and performing stirring for 3 hours. Water (560L) was added to the reaction solution, followed by extraction with dichloromethane (420L). The organic layer was dehydrated with anhydrous sodium sulfate (25 kg), and concentrated under reduced pressure to quantitatively obtain the title compound (11.04 kg) as a pale yellow oil.

[0154] 1 H NMR (CDCl 3 ,400MHz)δ3.62(t,2H),3.49(t,2H),2.05(m,2H)

[0155]

[0156] Step 2. Preparation of 1-(3-chloropropyl)-1H-1,2,3-triazole (formula 5)

[0157] Acetonitrile (96L) and potable water (53.L) were a...

Embodiment 2

[0160] [Example 2] Preparation of 3-(1H-1,2,3-triazol-1-yl) propyl methanesulfonate (formula 5)

[0161] The preparation of step 1.3-azidopropan-1-alcohol (formula 8)

[0162] Dimethylsulfoxide (1.3 L) was added to the reaction portion, and then 3-bromo-1-propanol (0.14 kg) was added thereto at room temperature. A reaction solution was prepared by adding sodium azide (58 g) thereto, washing the reaction part with dimethyl sulfoxide (0.2 L) and performing stirring for 3 hours. Water (5.6 L) was added to the reaction solution and the resulting solution was extracted with dichloromethane (4.2 L). The organic layer was dehydrated with anhydrous sodium sulfate (0.5 kg), and concentrated under reduced pressure to quantitatively obtain the title compound (0.11 kg) as an oil.

[0163] 1 H NMR (CDCl 3 ,400MHz)δ3.72(m,2H),3.42(m,2H),1.81(m,2H)

[0164]

[0165] Step 2. Preparation of 3-(1H-1,2,3-triazol-1-yl)propan-1-ol (Formula 5)

[0166] Acetonitrile (303 mL) and drinkin...

Embodiment 3

[0173] [Example 3] Preparation of 3-(1H-1,2,3-triazol-1-yl)propyl 4-methylbenzenesulfonate (formula 5)

[0174] Dichloromethane (49 mL) was added to the reaction portion, and then 3-(1H-1,2,3-triazol-1-yl)propan-1-ol (4.9 g) was added thereto. The reaction solution was cooled to 0°C to 10°C, triethylamine (10.8 mL) was added to the reaction solution, and 4-methylbenzenesulfonate (11.0 g) was slowly added thereto. The temperature of the resulting solution was raised to room temperature, and the solution was stirred for 2 hours. Drinking water (98 mL) was added to the resulting solution, followed by extraction with dichloromethane (146 mL), and concentration under reduced pressure. To the concentrated residue were added drinking water (75 mL) and charcoal (2.0 g), and stirred for 2 hours to prepare a mixed solution. The mixed solution was filtered through celite and extracted with dichloromethane (200 mL). The organic layer was washed with 5% NaCl aqueous solution, dehydrated...

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Abstract

The present invention relates to the preparation of N-[[1-{3-(1,2,3-triazol-1-yl)propyl}piperidine-4 as a novel benzamide derivative as a 5-HT4 receptor agonist - Base] methyl] -4-amino-5-chloro-2-methoxybenzamide or a pharmaceutically acceptable salt thereof; can be used for the preparation of novel intermediates of the compound; and the preparation of the intermediate Methods. The preparation method of the present invention can be used in mass production because inexpensive reagents and intermediates are used, and the number of reaction processes is reduced, thereby saving preparation cost and improving yield.

Description

technical field [0001] The present invention relates to the preparation of N-[[1-{3-(1,2,3-triazol-1-yl)propyl}piperidin-4-yl]methyl]-4- as benzamide derivatives A method of amino-5-chloro-2-methoxybenzamide or a pharmaceutically acceptable salt thereof; an intermediate useful in the preparation of said compound; and a method of preparing said intermediate. Background technique [0002] Serotonin (5-HT) is a neurotransmitter widely distributed in the body. Seven subtypes of serotonin receptors have been known so far, and great attention has been paid to identifying the 5-HT4 receptor as one of the seven subtypes and confirming the pharmacological action of the 5-HT4 receptor. Typically, 5-HT4 receptor agonists find use in the treatment of a variety of disorders such as gastroesophageal reflux disease, gastrointestinal disorders, gastric motility disorders, non-ulcer dyspepsia, functional dyspepsia, irritable bowel syndrome (IBS ), constipation, dyspepsia, esophagitis, gast...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/06A61K31/454A61P1/04
CPCC07D401/06A61P1/04A61P1/08A61P1/10A61P1/12A61P1/14A61P11/00A61P25/00A61P25/04A61P25/06A61P25/28A61P9/00A61P9/04A61P9/06A61P3/10C07C55/14C07C57/145C07C57/15C07C59/255C07C59/265
Inventor 郭祐宁李庚锡U·P·雷迪郑淳圭朴泰善林重仁
Owner 东亚ST 株式会社
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