Tag: M.W=500-600

Some common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: indolines-derivatives

Preparation of 3- {7-cyano-5 – [(2R) -2 – ({2- [2- (2,2,2- trifluoroethoxy) phenoxy] ethyl} Propyl benzoate fumaric acid salt A mixture of 3- {5- (2R) -2-aminopropyl} -7-cyano-2,3-dihydro-1H- (2R, 3R) -monotartaric acid salt (monotartaric acid salt of the compound of formula (2)), potassium carbonate (80 g), and a mixed solvent of acetonitrile and dimethylacetamide ACN / DMAC = 500 mL / 500 mL) was warmed to 80 & lt; 0 & gt; C and stirred for 30 min. To the reaction mixture, 70 g of 2- [2- (2,2,2-trifluoroethoxy) phenoxy] ethyl methanesulfonate (compound of formula (III)) and 9.70 g of KI were added, Lt; / RTI & gt; The reaction mixture was cooled to room temperature and extracted with 1 L of ethyl acetate and 1.5 L of water. The organic layer obtained by layer separation was washed with 1 L of brine, dried over 40 g of anhydrous MgSO4 for 30 minutes, and then washed again with 200 mL of ethyl acetate. 23 g of fumaric acid was added to the obtained organic layer, and the mixture was heated to 50 DEG C, cooled to room temperature, and stirred for 2 hours. reaction The mixture was filtered, and the resulting solid was washed with 200 mL of ethyl acetate and dried in vacuo to yield 113 g of the title compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 239463-85-5, its application will become more common.

Reference:
Patent; Dasan Medichem Co., Ltd; Ryu, Hyung Sun; Sin, Dong Kyun; Kim, Sung Ho; Ahn, Jin Woo; Jo, Hey Jung; Moon, Sung Chul; Aum, Woon Yong; Kim, Jae Hyung; (12 pag.)KR2016/27536; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 239463-85-5,Some common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

1. 80L water was added 200L reactor, adding sodium carbonate 6.2Kg stirring to clarify;2. Add ethyl acetate 50L, stirring,10 Kg of 5 – [(2R) -2-aminopropyl] -2,3-dihydro-1- [3- (benzoyloxy) propyl] -1H-indole-7-carbonitrile tartarate was added, Stir for 2 hours;3. Let stand liquid, the aqueous phase was extracted once with 20 L of ethyl acetate, the combined organic phase;The organic phase was washed twice with 15 L of saturated brine and the organic phase was dried over anhydrous sodium sulfate for 4 hours.5. Suction filtration, desiccant was washed with ethyl acetate; the solvent was dried under reduced pressure to give an oil 7Kg,Is 5 – [(2R) -2-aminopropyl] -2,3-dihydro-1- [3- (benzoyloxy) propyl] -1H-indole-7-carbonitrile, 99%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, its application will become more common.

Reference:
Patent; Beijing Tiantaihenghua Pharmaceutical Co., Ltd.; Li Xueqin; Liu Wenhui; (21 pag.)CN106995399; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 239463-85-5 as follows. Recommanded Product: (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate

Example 10: Preparation of 5-((R)-2-aminopropyl)-l-(3-hydroxypropyl) indoline- 7-carbonitrile of Formula ICTo a mixture of Tartrate salt of 3-(5-((R)-2-aminopropyl)-7-cyanoindolin-l-yl) propyl benzoate of Formula (I) (5 gm) in methanol (50 ml) and water (50 ml) was added potassium hydroxide and stirred the reaction mass for overnight at room temperature. The mixture was concentrated under reduced pressure and water (100 ml) was added. The mixture was extracted three times with 5% of Methanol: Methylene Dichloride (3 x 100 ml) and the combined organic layers were distilled to give 1.7 gm of 5-((R)-2- aminopropyl)- 1 -(3 -hydroxypropyl)indoline-7-carbonitrile of Formula IC.

According to the analysis of related databases, 239463-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PANACEA BIOTEC LTD; JAIN, Rajesh; RAO, Jagadeeshwar R; RAO, Siripragada Mahender; WO2012/131710; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 239463-85-5, Recommanded Product: (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate

3- {5 – [(2R) -2-aminopropyl] -7-cyano-2,3-dihydro -1H- indol-1-yl} propyl benzoate (2R, 3R) – mono tartrate 50g(97.5mmol, 1eq ) was poured into methanol 500ml, potassium hydroxide 12g (214mmol, 2.2eq)was reflux for 2 hours stirring was charged. After completion of the reaction, after cooling to room temperature filtered, the filtrate was concentrated (R)-5-(2-aminopropyl) -1- (3-hydroxypropyl) indoline-7-carbonitrile 25 g (100%) It was obtained.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyongbo Pharm Company Limited; Son, Feju; Ban, Sonfun; Kwon, Hyok Bom; Yoon, Ik Hwan; Choi, Min-sik; Yang, Jiwon; (15 pag.)JP2016/23186; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 239463-85-5,Some common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a slurry of SI-I (769 g, 1.50 mol) as the tartrate salt (e.e. 98.3%) in dichloromethane (2 L) was added dropwise an aqueous solution of sodium hydroxide (5 N, 126 g, 3.15 mol) at 10 C, all in a round bottom flask (5 L). The reaction mixture was stirred until the pH was 11. The organic layer was separated and the aqueous layer was extracted with dichloromethane twice (500 ml 2). The combined organic layer was washed with water to neutrality, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the SI-II (531 g, 97.5%, HPLC 98.2%) as a light yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, its application will become more common.

Reference:
Article; Liu, Hui; Lv, Fei; Liu, Yuan; Organic Preparations and Procedures International; vol. 51; 3; (2019); p. 287 – 293;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 239463-85-5, The chemical industry reduces the impact on the environment during synthesis 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, I believe this compound will play a more active role in future production and life.

A solution of 500 g of 5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1Hindole-7-nitrile tartrate (Compound SM1) was added to 3.0 L of dichloromethane with stirring, then,an aqueous solution (4.0 L) of potassium carbonate (1.105 kg) 221 g of (Boc) 2O, after completion ofthe dropwise addition, 15 to 25 C for 5 hours, standing still liquid, dichloromethane phase with 0.2mol / L HCl solution 3L, saturated sodium bicarbonate solution 2L, saturated brine 2L, then dried overanhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure to give457 g of compound V with an HPLC purity of 99.57%;

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Qilu Pharmaceutical Co., Ltd; Leng, Chuanxen; Fan, Chuanwen; Fang, Xi; Lin, Dong; Liu, Peiyuan; (14 pag.)CN106045892; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 239463-85-5,Some common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 9: Preparation of SilodosinProcedure 1: To a solution of Tartrate salt of 3-(5-((R)-2-aminopropyl)-7- cyanoindolin-l-yl) propyl benzoate (I) (50, 0.097 mol) in ethyl acetate (500 ml) was added water (500 ml) followed by addition of aqueous solution of Potassium carbonate (Potassium carbonate (130 g) dissolved in water (200 ml)). The mixture was stirred for lh at room temperature and the layers were separated. The organic layer was washed with water (500 ml) and concentrated under reduced pressure. The obtained crude was dissolved in Isopropyl alcohol (750 ml), Sodium carbonate (11.3 g, 0.107 mol) and 2- [2-(2,2,2-trifluoroethoxy)phenoxy]ethyl methane sulfonate of Formula XIII (36.7 g, 1.16 mol) were added. The mixture was stirred at 80C for 40-50 h. After completion of the reaction, the mixture was cooled and water (500 ml) was added. The organic layer was extracted with ethyl acetate twice (2 x 500 ml). The combined organic layers were evaporated to obtain the product and the product obtained was purified by column chromatography using dichloromethane and methanol in different ratios as a mobile phase. The appropriate fractions were combined together and distilled under reduced pressure to give 38 gm of 3-{7-cyano-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)- phenoxy]ethyl}amino)propyl)-2,3-dihy dro-lH-indol-l-yl) -propyl benzoate of Formula XIV (HPLC purity: 99.5%).The conversion of Formula XIV to Silodisn was followed by procedures disclosed in any of the prior art including United States patent application 20070197627 and United States patent 5,387,603.

The synthetic route of 239463-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PANACEA BIOTEC LTD; JAIN, Rajesh; RAO, Jagadeeshwar R; RAO, Siripragada Mahender; WO2012/131710; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, A new synthetic method of this compound is introduced below., Computed Properties of C26H31N3O8

Step S301: In a 500 mL three-necked bottle, respectively add 5.14 g of 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro -7-cyano-1H-indole tartrate, 150mL dichloromethane, 5mL triethylamine, and stir;After stirring and dissolving, 2.18 g of di-tert-butyl dicarbonate was added in portions, and the reaction was stirred at room temperature for 2 h to obtain a reaction solution;Add 100 mL of purified water to the above reaction solution, stir for 10 min, then stand still for layering;Wash the separated organic phase with 100 mL of purified water and 100 mL of saturated sodium chloride, and then dry the organic phase with anhydrous sodium sulfate for 2 h, and then filter to obtain a filtrate;The filtrate was concentrated under reduced pressure to obtain 3.92 g of light yellow oily compound II, which was 5-[(2R)-2-(tert-butoxycarbonyl)aminopropyl]-1-[3-(benzoyloxy ) Propyl]-2,3-dihydro-7-cyano-1H-indole, the yield of which is 84.48%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Beijing Xinkaiyuan Pharmaceutical Technology Co., Ltd.; Chai Guoju; Zhang Ding; Wu Yanpeng; Li Jing; Ge Zhimin; Dai Xinmin; (17 pag.)CN111116448; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 239463-85-5, Safety of (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate

3-{5-(2R)-2-aminopropyl}-7-cyano-{2,3-dihydro-1H-indol-1-yl}propylbenzoate(2R,3R)tartarate(Mono-tartaric acid salt of the compound of formula (II)),A mixture of potassium carbonate (80 g) and a mixed solvent of acetonitrile and dimethylacetamide (ACN / DMAC = 500 mL / 500 mL) was heated to 80 DEG C and stirred for 30 minutes. To the reaction mixture70 g of 2- [2- (2,2,2-trifluoroethoxy) phenoxy] ethyl methanesulfonate (compound of formula 3) and 9.70 g of KI were added,The reaction was carried out at the same temperature for 10 hours.The reaction mixture was cooled to room temperature, 1 L of ethyl acetate and 1.5 L of water were extracted.The organic layer obtained by layer separation was washed with 1 L of brine,After drying over 40 g of anhydrous MgSO4 for 30 minutes,After washing again with 200 mL of ethyl acetate, the solvent was removed by distillation.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Dasan Medichem Co.,Ltd; Ryu, Hyung Sun; Sin, Dong Kyun; Kim, Sung Ho; Ahn, Jin Woo; Jo, Hey Jung; Moon, Sung Chul; Aum, Woon Yong; Kim, Jae Hyung; (14 pag.)KR2016/27537; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 239463-85-5, A common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: 3- {5- (2R) -2-aminopropyl} -7-cyano-2,3-dihydro-1H-indol-1-yl}Propyl benzoate(2R, 3R) -mono-tartaric acid salt(Mono-tartaric acid salt of the compound of formula (II)),Potassium carbonate (80 g),And a mixed solvent of acetonitrile and dimethylacetamide (ACN / DMAC = 500 mL / 500 mL) was heated to 80 DEG C,Stir for 30 min. To the reaction mixture were added 70 g of 2- [2- (2,2,2-trifluoroethoxy) phenoxy] ethyl methanesulfonate (compound of formula 3) and 9.70 g of KI,The reaction was carried out at the same temperature for 10 hours.The reaction mixture was cooled to room temperature,And extracted with 1 L of ethyl acetate and 1.5 L of water.The organic layer obtained by layer separation was washed with 1 L of brine,After drying over 40 g of anhydrous MgSO4 for 30 minutes,After washing again with 200 mL of ethyl acetate, the solvent was removed by distillation. 400 mL of methanol, 100 mL of water and 20 g of KOH were added to the obtained residue. After the mixture was stirred at room temperature for 10 hours,1 L of ethyl acetate and 1 L of water were added and extracted for 10 minutes.The organic layer obtained by layer separation was washed sequentially with 1 L of saturated aqueous solution and 1 L of saturated brine,After drying over 40 g of anhydrous MgSO4 for 30 minutes,After washing with 200 mL of ethyl acetate,18 g of oxalic acid was added.The reaction mixture was stirred at 50 for 30 minutes, It cooled to room temperature.600 mL of isopropyl ether was added to the reaction mixture,Stirred for 2 hours, and then filtered.The obtained crystals were washed with 200 mL of isopropyl ether,At 40 for 10 hours to give the titled compound as a dried in vacuo to 88 g.The reaction was carried out in the same manner as in Example 1, except that 23.5 g of fumaric acid was used instead of oxalic acid to obtain 92 g of the title compound.Yield: 81%Purity: 99.5%Impurities (dimer): Not more than 0.1%

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Dasan Medichem Co., Ltd.; Ryu, Hyung Sun; Sin, Dong Kyun; Kim, Sung Ho; Ahn, Jin Woo; Kim, Jae Hyung; Aum, Woon Yong; (12 pag.)KR2016/92976; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem