1,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

Base Information

• Chemical Name: 1,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-one
• CAS No.: 32501-05-6
• Molecular Formula: C7H6N2O
• Molecular Weight: 134.137
• Hs Code.: 2933990090
• NSC Number: 244253
• DSSTox Substance ID: DTXSID70311594
• Nikkaji Number: J88.811G
• Wikidata: Q72466143
• Mol file: 32501-05-6.mol

Synonyms:32501-05-6;1H-Pyrrolo[3,2-b]pyridin-2(3H)-one;1,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-one;1,3-dihydropyrrolo[3,2-b]pyridin-2-one;4-Azaoxindole;1H,2H,3H-pyrrolo[3,2-b]pyridin-2-one;MFCD02179615;1,3-Dihydro-2H-pyrrolo(3,2-b)pyridin-2-one;4-Azaindol-2(3H)-one;dihydropyrrolopyridone;NSC244253;2H-PYRROLO[3,2-B]PYRIDIN-2-ONE, 1,3-DIHYDRO-;NSC 244253;SCHEMBL659375;DTXSID70311594;SC3121;AKOS006278279;CCG-339743;NSC-244253;PB29192;AC-24386;DS-13132;SY008091;1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one;1,3-Dihydropyrrolo[3,2-b]pyridine-2-one;AM20050801;CS-0044058;FT-0684659;EN300-106032;1,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-one #;A821302;J-503907;W-205488;Z1198159859

Chemical Property of 1,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 204-206 °C
• Refractive Index: 1.594
• Boiling Point: 336.9 °C at 760 mmHg
• PKA: 12.84±0.20(Predicted)
• Flash Point: 157.6 °C
• PSA: 41.99000
• Density: 1.286 g/cm³
• LogP: 0.71420
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 134.048012819
• Heavy Atom Count: 10
• Complexity: 158

Purity/Quality:

99%, ^*data from raw suppliers

1H-Pyrrolo[3,2-B]pyridin-2(3H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(C=CC=N2)NC1=O

Technology Process of 1,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

There total 1 articles about 1,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-one 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: 34.0%

ethyl 2-(3-(3-phenylureido)pyridin-2-yl)acetate → 2-hydroxy-N1,N3-diphenyl-1H-pyrrolo[3,2-b]pyridine-1,3-dicarboxamide + 1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one (32501-05-6)

Guidance literature:

With potassium carbonate; In acetonitrile; at 60 ℃;

DOI:10.1016/j.tet.2014.11.057

Reference yield: 64.0%

2-fluoro-3-chlorobenzaldehyde (85070-48-0) + 1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one (32501-05-6) → E/Z-3-(3-chloro-2-fluorobenzylidene)-1,3-dihydropyrrolo[3,2-b]pyridin-2-one (1360821-93-7)

Guidance literature:

With piperidine; In methanol; at 50 ℃;

Reference yield:

1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one (32501-05-6) → methyl rac-4-((2S,3S,4S,5R)-4-(3-chloro-2-fluorophenyl)-2-neopentyl-2'-oxo-1',2'-dihydrospiro[pyrrolidine-3,3'-pyrrolo[3,2-b]pyridine]-5-ylcarboxamido)-3-methoxybenzoate

Guidance literature:

Multi-step reaction with 2 steps

1.1: piperidine / methanol / 50 °C

2.1: lithium hydroxide / tetrahydrofuran / 0.17 h / 40 °C

2.2: 20 h / 40 °C

With piperidine; lithium hydroxide; In tetrahydrofuran; methanol;

Downstream raw materials:

GW441756

E/Z-3-(3-chloro-2-fluorobenzylidene)-1,3-dihydropyrrolo[3,2-b]pyridin-2-one

Refernces

Discovery of potent and orally active p53-MDM2 inhibitors RO5353 and RO2468 for potential clinical development

10.1021/ml400359z

The research aims to develop small-molecule MDM2 inhibitors to restore dysfunctional p53 activities for cancer treatment. The study builds on previous work on a non-imidazoline MDM2 inhibitor, RG7388, and explores additional derivatives to expand chemodiversity and identify potent and selective MDM2 antagonists with desirable pharmacological properties. The researchers focused on bioisosteric replacements of the 6-chlorooxindole group in RO8994, leading to the identification of two highly potent, selective, and orally active p53-MDM2 inhibitors, RO2468 and RO5353. These compounds demonstrated excellent in vitro and in vivo pharmacokinetic profiles and significant tumor regression in mouse models at doses comparable to RO8994. The key chemicals used in the research include RO8994, RO2468 (14), and RO5353 (16), along with various analogues such as 4-azaoxindole (I), 5-azaoxindole (II), 7-azaoxindole (III), 2-chloropyrrolo[2,3-d]pyrimidin-6-one (IV), and 2-chlorothienyl[3,2-b]pyrrol-5-one (V). The study concludes that RO2468 and RO5353 have promising potential for clinical development.

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