Method for preparing 3-(dipropyl amino)-4-methoxyl benzenesulfonic acid

A technology of methoxybenzenesulfonic acid and dipropylamino, which is applied in the field of preparation of 3--4-methoxybenzenesulfonic acid, and achieves the effects of simple preparation process, low cost and high yield

Active Publication Date: 2014-09-03
上海毕得医药科技股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the synthetic method of 3-(dipropylamino)-4-methoxybenzenesulfonic acid has not been reported in the literature, but it is of great significance to study its synthetic method

Method used

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  • Method for preparing 3-(dipropyl amino)-4-methoxyl benzenesulfonic acid
  • Method for preparing 3-(dipropyl amino)-4-methoxyl benzenesulfonic acid
  • Method for preparing 3-(dipropyl amino)-4-methoxyl benzenesulfonic acid

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Embodiment

[0025] figure 1 Be 3-(dipropylamino)-4-methoxybenzenesulfonic acid synthetic route of the present invention, concrete steps are:

[0026] Step 1 Dissolve 2-methoxyaniline (40 g, 0.325 mol) in dimethyl sulfoxide (200 ml) into a three-neck flask, then add potassium carbonate (134.79 g, 0.974 mol), n-propane bromide ( 117.9 g, 0.974 mol), heated to reflux, reacted at 80°C for 16 hours, and detected by TLC (thin layer chromatography). secondary. The organic phases were combined, washed twice with saturated brine (200ml), the organic phase was dried with anhydrous Na2SO4, filtered, the organic phase was concentrated under reduced pressure, and the crude product was purified by column chromatography to obtain the compound 2-methoxy-N,N- 50.5 g of dipropylaniline, the yield is about 75%. 1H NMR (600 MHz, DMSO) δ6.91 – 6.86 (m, 1H), 6.85 – 6.79 (m, 0H), 3.76 (d, J = 11.8 Hz, 1H), 3.05 –2.89 (m, 1H), 1.45 – 1.25 (m, 4H), 0.91 – 0.70 (m, 2H).

[0027] In this reaction step, the pro...

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Abstract

The invention belongs to the field of chemical synthesis, and discloses a method for preparing 3-(dipropyl amino)-4-methoxyl benzenesulfonic acid. The 3-(dipropyl amino)-4-methoxyl benzenesulfonic acid takes 2-anisidine as the raw material and is prepared through two steps of reaction. The invention provides the synthesis method for the 3-(dipropyl amino)-4-methoxyl benzenesulfonic acid for the first time, and offers the synthesis route for preparation of the 3-(dipropyl amino)-4-methoxyl benzenesulfonic acid; and the preparation method is simple, has high yield and low cost, and can be used for large-scale production.

Description

Technical field: [0001] The invention relates to an important intermediate of a compound with CaSR (calcium receptor) agonistic activity, especially a preparation method of 3-(dipropylamino)-4-methoxybenzenesulfonic acid. Background technique: [0002] Calcium receptors are also known as calcium sensing receptors (Calcium sensing receptor, also known as "CaSR"), in 1993 as G protein-coupled 7 transmembrane receptors (G-protein couple G-Protein Coupled Receptor, GPCR) was cloned from bovine thyroid. Calcium receptors sense extracellular Ca2+ to change the intracellular Ca2+ concentration, and thus have the function of regulating the production of hormones such as thyroid hormones involved in the regulation of Ca2+ metabolism. [0003] In recent years, it has been found that cinacalcet (CCT), as a calcium receptor agonist, increases the Ca2+ sensitivity of calcium receptors by acting on the calcium receptors of the parathyroid gland, and has the effect of inhibiting the sec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/06C07C309/49
Inventor 李进飞李新玲黄亮富
Owner 上海毕得医药科技股份有限公司
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