74420-06-7

Basic information

• Product Name: 1H-Pyrrolo[2,3-b]pyridine, 4-nitro-, 7-oxide
• Synonyms: 1H-Pyrrolo[2,3-b]pyridine, 4-nitro-, 7-oxide;4-Nitro-7-oxide-7-azaindole ,97%;4-nitro-1H-pyrrolo[2,3-b]pyridine 7-oxide;4-nitro-7H-1$l^{5},7-pyrrolo[2,3-b][1$l^{5}]pyridin-1-one;4-nitro-7-oxide-7-azaindole;1H-Pyrrolo[2,3-b]pyridine, 4-nitro-, 7-oxide-2;4‐nitro‐1h‐pyrrolo[2,3‐b]pyridin‐7‐ium‐7‐olate;7-hydroxy-4-nitropyrrolo[2,3-b]pyridine
• CAS NO: 74420-06-7
• Molecular Formula: C₇H₅N₃O₃
• Molecular Weight: 179.13
• Mol File: 74420-06-7.mol

Chemical Properties

• Melting Point: 229-230.5 °C (decomp)
• Boiling Point: 463.331 °C at 760 mmHg
• Flash Point: 234.015 °C
• Appearance: /
• Density: 1.684 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.748
• PKA: 10.45±0.40(Predicted)
• CAS DataBase Reference: 1H-Pyrrolo[2,3-b]pyridine, 4-nitro-, 7-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[2,3-b]pyridine, 4-nitro-, 7-oxide(74420-06-7)
• EPA Substance Registry System: 1H-Pyrrolo[2,3-b]pyridine, 4-nitro-, 7-oxide(74420-06-7)

Safety Data

• Statements: 20/21/22
• Safety Statements: 24/25-36/37
• Hazardous Substances Data: 74420-06-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellow solid

InChI:InChI=1/C7H5N3O3/c11-9-4-2-6(10(12)13)5-1-3-8-7(5)9/h1-4,8H

Upstream product

• 74420-10-3 1H-pyrrolo<2,3-b>pyridine-3-carboxamide 7-oxide 
• 55052-24-9 1H-Pyrrolo[2,3-b]pyridine-7-oxide 
• 271-63-6 7-Azaindole 

Downstream Products

• 83683-82-3 4-nitro-1H-pyrrolo<2,3-b>pyridine 
• 688781-87-5 6-chloro-4-nitro-1H-pyrrolo[2,3-b]pyridine 
• 688781-75-1 3-fluoro-4-((1H-pyrrolo [2,3-b]pyridin-4-yl)oxy)aniline 
• 688781-89-7 {4-[(6-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}amine 
• 869335-22-8 6-chloro-4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine 
• 881902-82-5 3-fluoro-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy]-phenylamine 
• 881902-81-4 4-[6-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy]-3-fluoro-phenylamine 
• 869335-30-8 (6-chloro-1-([2-(trimethylsilyl)ethoxy]methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)(2-fluoro-4-nitrophenyl)acetic acid methyl ester 
• 83683-90-3 4-amino-N1-(β-D-ribofuranosyl)-pyrrolo[2,3-b]pyridine 
• 869335-36-4 3-Bromo-4-nitro-1H-pyrrolo[2,3-b]pyridine 
• 688782-67-4 benzyl 3-(2-amino-6-{[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino}-pyrimidin-4-yl)piperidine-1-carboxylate 
• 55052-28-3 4-chloro-7-azaindole 
• 688781-37-5 N₄-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-6-piperidin-3-ylpyrimidine-2,4-diamine 

Relevant articles and documents

Improved synthesis of the selective rho-kinase inhibitor 6-chloro-n4-{3,5-difluoro-4-[(3-methyl-1h-pyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl} pyrimidin-2,4-diamine

A highly potent and selective Rho-kinase inhibitor containing a 7-azaindole moiety has been developed at Bayer Schering Pharma. Herein we disclose details of a significantly improved synthesis of the compound in 8.2% overall yield. Key aspects include cost and safety considerations and the uncommon use of a trifluoromethyl group with controllable reactivity as a masked methyl group.

Substituted Phenylamino-Pyrimidines

The invention relates to substituted phenylaminopyrimidines, to a process for their preparation and to their use for preparing medicaments for the treatment and/or prophylaxis of diseases in humans and animals, in particular cardiovascular disorders.

HETARYLOXY-SUBSTITUTED PHENYLAMINO PYRIMIDINES AS RHO KINASE INHIBITORS

The invention relates to hetaryloxy-substituted phenylamino pyrimidines, a method for the production thereof, and the use thereof for producing medicaments utilized for the treatment and/or prevention of diseases in humans and animals, particularly cardiovascular diseases.

SUBSTITUTED PHENYLAMINO-PYRIMIDINES

The invention relates to substituted phenylamino-pyrimidines, to a method for their production and to their use for producing medicaments for the treatment and/or prophylaxis of diseases in humans and animals, in particular for the treatment of cardiovascular diseases.

HETEROARYLOXY-SUBSTITUTED PHENYLAMINOPYRIMIDINES AS RHO-KINASE INHIBITORS

The invention relates to heteroaryloxy-substituted phenylaminopyrimidines, to methods for the production thereof, and to the use of the same for producing medicaments for the treatment and/or prophylaxis of diseases, especially cardiovascular diseases. The inventive compounds inhibit Rho-kinase.

Synthesis of 4-Amino-1H-pyrrolopyridine (1,7-Dideazaadenine) and 1H-Pyrrolopyridin-4-ol (1,7-Dideazahypoxanthine)

4-Amino-1H-pyrrolopyridine (1,7-dideazaadenine) (5) has been synthesized by the iron and acetic acid reduction of 4-nitro-1H-pyrrolopyridine 7-oxide (13), obtained by nitration of 1H-pyrrolopyridine-3-carboxamide 7-oxide (17).Other nitration reactions in the 1H-pyrrolopyridine 7-oxide series are disclosed.The preparation of 1H-pyrrolopyridin-4-ol (1,7-dideazahypoxanthine) (6) began with the hydrolysis of ethyl 1-benzyl-3-cyano-4-oxo-4,7-dihydro-1H-pyrrolopyridine-5-carboxylate (21) to the 3,5-dicarboxylic acid derivative of 1-benzyl-4-oxo-4,7-dihydro-1H-pyrrolopyridine (22).Decarboxylation of 22 with subsequent debenzylation formed 6.