1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile Chemical Properties

Melting point:

73-75°C

Boiling point:

608.6±55.0 °C(Predicted)

Density 

1.27

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

7.80±0.13(Predicted)

form 

Solid

color 

Light Yellow to Yellow

1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile Usage And Synthesis

Uses

3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl Benzoate is used in the preparation of Silodosin (S465000), an α1a-adrenoceptor antagonist. It is used in treatment of benign prostatic hypertophy.

Synthesis

1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carboxaldehyde (20.0 g) was used as a starting material and dissolved in tetrahydrofuran (29.0 ml). To this solution, hydroxylamine hydrochloride (4.21 g) and pyridine (16.0 ml) were added sequentially. The reaction mixture was stirred at a constant temperature at 50 °C for 2 h. Acetic anhydride (9.0 ml) was subsequently added. Stirring of the reaction mixture was continued at 80°C for 2 hours. After completion of the reaction, extraction was carried out with toluene. The toluene layer obtained by extraction was washed with dilute hydrochloric acid, after which the solvent was removed by distillation under reduced pressure to give 16.0 g of propyl 3-(7-cyano-5-(2-nitropropyl)dihydroindol-1-yl)benzoate (Compound XX).

References

[1] Patent: WO2011/124704, 2011, A1. Location in patent: Page/Page column 19-20
[2] Patent: WO2013/56842, 2013, A1. Location in patent: Page/Page column 19
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 8, p. 3826 - 3839

1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile(350797-56-7)Related Product Information

• Silodosin Impurity 18
• Silodosin β-D-Glucuronide N-Carboxybenzyl O-Methyl Tri-acetate
• Silodosin Impurity 26
• NCFJJNFEEPMRAQ-XMMPIXPASA-N
• Silodosin
• 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate
• Silodosin
• 1H-Indole-7-carbonitrile, 2,3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]aMino]propyl]-
• O-Acetyl Silodosin
• 1-(3-Hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]aMino]propyl]-1H-indole-7-carboxaMide
• Silodosin Carboxylic Acid Impurity
• (R)-5-(2-((2-(2-ethoxyphenoxy)ethyl)amino)propyl)-1-(3-hydroxypropyl)indoline-7-carboxamide(WXG00186)
• Silodosin β-D-Glucuronide Sodium Salt
• Silodosin Glucuronide
• Silodosin-d4 (Chiral)
• 5-(2-Aminopropyl)-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile
• Silodosin Impurity 33
• Silodosin-d6