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Preparation method of 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxyl) benzene sulfonyl chloride)-1H-pyrrole-3-yl)-N-methyl amine

A technology of methoxypropoxy and methoxypropoxy, applied in 1‑(5‑(2‑fluorophenyl)‑1‑3‑(3‑methoxypropoxy)benzenesulfonyl chloride)‑ The preparation field of 1H-pyrrole-3-yl)-N-methylamine can solve the problems of slow onset of acid breakthrough at night, instability, influence of administration time, etc.

Active Publication Date: 2018-04-06
JIANGSU CAREFREE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Such as: the influence of administration time on drug efficacy; slow onset of acid breakthrough at night; instability under acidic conditions (need to be formulated into intestinal preparations); dependence on CYP450 enzymes (resulting in significant individual differences), etc.

Method used

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  • Preparation method of 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxyl) benzene sulfonyl chloride)-1H-pyrrole-3-yl)-N-methyl amine
  • Preparation method of 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxyl) benzene sulfonyl chloride)-1H-pyrrole-3-yl)-N-methyl amine
  • Preparation method of 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxyl) benzene sulfonyl chloride)-1H-pyrrole-3-yl)-N-methyl amine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Preparation of 5-(2-fluorophenyl)-1-((3-(3-methoxypropoxy)benzenesulfonyl)-1H-pyrrole-3-carbaldehyde (compound 2)

[0021]

[0022] In a 10L reaction flask, add 60% NaH (300g, 7.62mol) to a solution of 1-1 (480g, 2.54mol) in THF (200ml), stir at -30°C for 25 min, add dropwise compound 1 (800g, 3.06 mol), stirred at -30°C for 10 min. The reaction solution was poured into 5L of ice water and extracted with ethyl acetate (2.5Lx3). The combined organic phase was dried, concentrated, added 1.5 ethanol and stirred for 1 h, suction filtered, and vacuum-dried to obtain a light yellow Solid 700g (66% yield).

Embodiment 2

[0023] Example 2: Preparation of 5-(2-fluorophenyl)-1-((3-(3-methoxypropoxy)benzenesulfonyl)-1H-pyrrole-3-carbaldehyde (compound 2)

[0024]

[0025] In a 2L reaction flask, dissolve compound 1-1 (95g, 0.5mol) in DMF (1000ml), add sodium tert-butoxide (96g, 1mol), stir for 25 min, and add compound 1 (158g, 0.6mol) dropwise , and stirred at 25°C for 1 hour. The reaction solution was cooled to room temperature, filtered with suction, concentrated to dryness under reduced pressure, and 80 g of a light yellow solid was obtained by column chromatography (yield 38.2%).

Embodiment 3

[0026] Example 3: Preparation of 5-(2-fluorophenyl)-1-((3-(3-methoxypropoxy)benzenesulfonyl)-1H-pyrrole-3-carbaldehyde (compound 2)

[0027]

[0028] In a 2L reaction flask, dissolve compound 1-1 (95g, 0.5mol) in acetonitrile (1000ml), add N, N-diisopropylethylamine (97g, 0.75mol), stir at room temperature for 20 min, drop Compound 1 (158g, 0.6mol) was stirred at room temperature for 1 hour. The reaction solution was cooled and then concentrated to dryness under reduced pressure. Column chromatography gave 68g of a light yellow solid (yield 32.4%).

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Abstract

The invention provides a preparation method of 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxyl) benzene sulfonyl chloride)-1H-pyrrole-3-yl)-N-methyl amine on the basis of the prior art. Reaction steps such as ulfoamidation and reductive amination are carried out on 3-(3-methoxypropoxyl) benzene sulfonyl chloride, so that the 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxyl) benzene sulfonyl chloride)-1H-pyrrole-3-yl)-N-methyl amine is obtained. The preparation method is short in reaction period, a high-toxicity reagent is avoided, and treatment operation is simplified, so that the preparation methodprovided by the invention can be used for obtaining the 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxyl) benzene sulfonyl chloride)-1H-pyrrole-3-yl)-N-methyl amine in large scale with high efficiency andlow cost.

Description

technical field [0001] The present invention relates to new chemical entities 1-(5-(2-fluorophenyl)-1-3-(3-methoxypropoxy)benzenesulfonyl chloride)-1H-pyrrol-3-yl)-N-methyl Methods for the preparation of amines. Background technique [0002] Since 1988, proton pump inhibitors represented by omeprazole have been widely used clinically to treat peptic ulcer, reflux esophagitis and Zoller-Ellison syndrome by inhibiting gastric acid secretion. Long-term clinical application has found that existing proton pump inhibitors still have limitations in terms of pharmacokinetics and pharmacodynamics. Such as: the effect of administration time on drug efficacy; slow onset of acid breakthrough at night; instability under acidic conditions (need to be formulated into intestinal preparations); dependence on CYP450 enzymes (resulting in significant individual differences), etc. [0003] Potassium-Competitive Acid Blockers (P-CABs) work by competitively inhibiting K+ in H+ / K+-ATPase through...

Claims

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Application Information

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IPC IPC(8): C07D207/48
CPCC07D207/48
Inventor 苏梅刘飞金秋
Owner JIANGSU CAREFREE PHARM CO LTD
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