5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate

Base Information

• Chemical Name: 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate
• CAS No.: 239463-85-5
• Molecular Formula: C22H25N3O2^.C4H6O6
• Molecular Weight: 513.547
• Mol file: 239463-85-5.mol

Synonyms:3-{5[(2R)-2-aminoprppyl]-7-cyano-2,3-dihydro-1H-indol-1-yl}propyl benzoate monotartaric acid salt; (R)-5-(2-aminopropyl)-1-(3-benzoyloxypropyl) Indoline-7-Carbonitrile Tartaric acid; 5-[(2R)-2-AMINOPROPYL]-1-[3-(BENZOYLOXY)PROPYL]-2,3-DIHYDRO-1H-INDOLE-7-CARBONITRILE (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE; (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate; 3-(5-((R)-2-aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate L-tartrate; 1-(3-benzoyloxypropyl)-7-cyano-5-(2-aminopropyl)-2,3-dihydroindole; 查看更多英文别名 收起

Chemical Property of 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate

Chemical Property:

• PSA: 194.41000
• LogP: 1.70028
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly, Sonicated), Ethanol (Slightly, Heated, Sonicated), Methanol (Sli

Purity/Quality:

5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile(2R,3R)-2,3-Dihydroxybutanedioate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-Dihydroxybutanedioate is an intermediate of Silodosin (S465000) which is an α1a-adrenoceptor antagonist and used in the treatment of benign prostatic hypertophy.

Technology Process of 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate

There total 62 articles about 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 33.3%

L-Tartaric acid (87-69-4,138508-61-9) + C38H39N3O4 → 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt (239463-85-5)

Guidance literature:

C₃₈H₃₉N₃O₄; With palladium on activated charcoal; hydrogen;

L-Tartaric acid; Inert atmosphere;

Reference yield: 30.9%

L-Tartaric acid (87-69-4,138508-61-9) + C42H41N3O4 → 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt (239463-85-5)

Guidance literature:

C₄₂H₄₁N₃O₄; With palladium on activated charcoal; hydrogen;

L-Tartaric acid; Inert atmosphere;

Reference yield: 23.5%

L-Tartaric acid (87-69-4,138508-61-9) + 3-(5-(2-((tert-butoxycarbonyl)amino)propyl)-7-cyanoindolin-1-yl)propylbenzoate → 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt (239463-85-5)

Guidance literature:

3-(5-(2-((tert-butoxycarbonyl)amino)propyl)-7-cyanoindolin-1-yl)propylbenzoate; With hydrogenchloride; In chloroform; water; at 25 - 30 ℃; for 5h;

L-Tartaric acid; In water; acetone; at 20 - 25 ℃; for 12h;

upstream raw materials:

L-Tartaric acid

5-(2-aminopropyl)-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole

1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole

1-(3-benzoyloxypropyl)-5-(2-nitro-1-propenyl)-2,3-dihydroindole

Downstream raw materials:

2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[[2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile

5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile

silodosin

Refernces

• 1、 -. "Preparation method of silodosin intermediate". . . Retrieved 2019/02/19.
• 2、 Zhao, Fei,Li, Jing,Chen, Ying,Tian, Yanxin,Wu, Chenglin,Xie, Yanan,Zhou, Yu,Wang, Jiang,Xie, Xin,Liu, Hong. "Design, Synthesis, and Biological Evaluation of Indoline and Indole Derivatives as Potent and Selective α1A-Adrenoceptor Antagonists". . p. 3826 - 3839. Retrieved 2016/05/24.