179386-43-7

Basic information

• Product Name: Sumanirole maleate
• Synonyms: (5R)-5,6-Dihydro-5-(MethylaMino)-4H-iMidazo[4,5,1-ij]quinolin-2(1H)-one (2Z)-2-Butenedioate;(R)-5,6-Dihydro-5-(MethylaMino)-4H-iMidazo[4,5,1-ij]quinolin- 2(1H)-one (2Z)-2-Butenedioate;(R)-5-(MethylaMino)-5,6-dihydro-1H-iMidazo[4,5,1-ij]quinolin-2(4H)-one Maleate,(free base);4H-IMidazo[4,5,1-ij]quinolin-2(1H)-one,5,6-dihydro-5-(MethylaMino)-, (5R)-;(5R)-5,6-Dihydro-5-(methylamino)-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one;Sumanirole
• CAS NO: 179386-43-7
• Molecular Formula: C₁₁H₁₃N₃O
• Molecular Weight: 319.31258
• Mol File: 179386-43-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Density: 1.32
• Refractive Index: 1.666
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: Sumanirole maleate(CAS DataBase Reference)
• NIST Chemistry Reference: Sumanirole maleate(179386-43-7)
• EPA Substance Registry System: Sumanirole maleate(179386-43-7)

Safety Data

• Hazardous Substances Data: 179386-43-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Light Beige Solid

Uses

Sumanirole is a high affinity D2 receptor agonist (EC50 values are between 17 and 75 nM in cell-based assays). Sumanirole displays >200-fold selectivity for the D2 receptor against other dopamine rece ptor subtypes (Ki values are 9.0, 1940, >2190 and >7140 for D2, D3, D4 and D1 receptors respectively). Sumanirole exhibits antiParkinsonian activity similar to Ropinirole (R641000).

InChI:InChI=1/C11H13N3O/c1-12-8-5-7-3-2-4-9-10(7)14(6-8)11(15)13-9/h2-4,8,12H,5-6H2,1H3,(H,13,15)/t8-/m1/s1

Upstream product

• 1171118-85-6 tert-butyl (2R,3S)-2-formyl-3-(2-nitrophenyl)aziridine-1-carboxylate 
• 1171119-05-3 1-(tert-butyl) 2-methyl (2R,3S)-3-(2-nitrophenyl)aziridine-1,2-dicarboxylate 
• 639478-61-8 tert-butyl (R)-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)carbamate 
• 1187928-12-6 tert-butyl (R)-(1,2,3,4-tetrahydroquinolin-3-yl)carbamate 
• 1644493-04-8 tert-butyl (R)-(1-(methoxycarbamoyl)-1,2,3,4-tetrahydroquinolin-3-yl)carbamate 
• 1623784-90-6 tert-butyl (R)-(1-methoxy-2-oxo-1,2,5,6-tetrahydro-4H-imidazo[4,5,1-ij]quinolin-5-yl)carbamate 
• 1623784-91-7 tert-butyl (R)-(1-methoxy-2-oxo-1,2,5,6-tetrahydro-4H-imidazo[4,5,1-ij]quinolin-5-yl)(methyl)carbamate 
• 186320-51-4 tert-butyl (R)-methyl(2-oxo-1,2,5,6-tetrahydro-4H-imidazo[4,5,1-ij]quinolin-5-yl)carbamate 
• 1466-88-2 2-nitrocinnamaldehyde 
• 185943-21-9 (R)-8-Azido-3-(benzyl-methyl-amino)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester 
• 185943-22-0 (R)-8-Amino-3-(benzyl-methyl-amino)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester 
• 185943-17-3 (R)-3-(Benzyl-methyl-amino)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester 
• 185943-04-8 (3R,4R)-3-Hydroxy-4-methylamino-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester 
• 185943-08-2 (1aR,7bS)-1a,7b-Dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid tert-butyl ester 

Relevant articles and documents

Experiences with commercial production scale operation of dissolving metal reduction using lithium metal and liquid ammonia

The final step which generates free base in the synthesis of Sumanirole Maleate (PNU-95666E) consists of a cryogenic dissolving metal reduction using lithium metal and liquid ammonia. This chemistry was new to the Pfizer API production plant. Due to the hazards associated with the handling of lithium metal and ammonia gas at cryogenic reaction temperature, special challenges were encountered related to the design of the equipment, choice and handling of materials, operations, waste treatment, and both safety and economic issues. The topics discussed in this article include the use of Li instead of Na or K, impact of the choice of physical form of lithium metal, design of the lithium addition apparatus, and problems experienced during the addition. We also discuss techniques for addition of ammonia to the reactor, evaporation of ammonia from the reaction mixture, options for ammonia disposal, and internal reuse of ammonia. Comments on hazards for this reaction are also provided. It is hoped that this document will be of benefit to other professionals who may want to develop and scale-up dissolving metal reduction processes.

Enantioselective synthesis of (R)-Sumanirole using organocatalytic asymmetric aziridination of an α,β-unsaturated aldehyde

Herein we report an enantioselective synthesis of (R)-Sumanirole wherein an organocatalytic asymmetric aziridination of 2-nitrocinnamaldehyde was the key step.

Synthesis of the Selective D2 Receptor Agonist PNU-95666E from D-Phenylalanine Using a Sequential Oxidative Cyclization Strategy

Compound 1 (PNU-95666E) is a selective and high-affinity agonist at the dopamine D2 receptor subtype and is of interest as a potential agent for the treatment of Parkinson's disease. Requiring a synthetic route amenable to scale-up, a synthesis