3-(9-Fluoro-2-(piperidine-1-carbonyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)-4-(imidazo[1,2-a]pyridin-3-yl)-1H-pyrrole-2,5-dione

Base Information

• Chemical Name: 3-(9-Fluoro-2-(piperidine-1-carbonyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)-4-(imidazo[1,2-a]pyridin-3-yl)-1H-pyrrole-2,5-dione
• CAS No.: 603288-22-8
• Molecular Formula: C28H25FN6O3
• Molecular Weight: 512.53
• UNII: 822M3GYM67
• DSSTox Substance ID: DTXSID90209085
• Nikkaji Number: J2.867.237C
• Wikidata: Q27082598
• NCI Thesaurus Code: C116849
• Pharos Ligand ID: 8PZL32HN9A98
• Metabolomics Workbench ID: 152993
• ChEMBL ID: CHEMBL362558
• Mol file: 603288-22-8.mol

Synonyms:3-(9-fluoro-2-(piperidin-1-ylcarbonyl)-1,2,3,4-tetrahydro(1,4)diazepino(6,7,1-hi)indol-7-yl)-4-imidazo(1,2-a)pyridin-3-yl-1H-pyrrole-2,5-dione;LY2090314

Chemical Property of 3-(9-Fluoro-2-(piperidine-1-carbonyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)-4-(imidazo[1,2-a]pyridin-3-yl)-1H-pyrrole-2,5-dione

Chemical Property:

• PKA: 7.41±0.60(Predicted)
• PSA: 95.44000
• Density: 1.55±0.1 g/cm3(Predicted)
• LogP: 3.56850
• Storage Temp.: -20°C
• Solubility.: insoluble in H2O; ≥91 mg/mL in DMSO; ≥4.27 mg/mL in EtOH with gentle warming and ultrasonic
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 512.19721684
• Heavy Atom Count: 38
• Complexity: 1030

Purity/Quality:

98%,99%, ^*data from raw suppliers

LY 2090314 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(CC1)C(=O)N2CCN3C=C(C4=CC(=CC(=C43)C2)F)C5=C(C(=O)NC5=O)C6=CN=C7N6C=CC=C7
• Recent ClinicalTrials: A Study of LY2090314 in Patients With Advanced or Metastatic Cancer
• Uses: LY 2090314 is a novel glycogen synthase kinase-3α inhibitor for the treatment of acute myeloid leukemia.

Technology Process of 3-(9-Fluoro-2-(piperidine-1-carbonyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)-4-(imidazo[1,2-a]pyridin-3-yl)-1H-pyrrole-2,5-dione

There total 18 articles about 3-(9-Fluoro-2-(piperidine-1-carbonyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)-4-(imidazo[1,2-a]pyridin-3-yl)-1H-pyrrole-2,5-dione 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: 81.0%

2-(imidazo-[1,2-a]pyridin-3-yl)acetamide (21801-86-5) + methyl 2-(9-fluoro-2-(piperidine-1-carbonyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)-2-oxoacetate (1239017-87-8) → LY2090314 (603288-22-8)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 5 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol101405g

Reference yield: 60.0%

piperidine carbamoyl chloride (13939-69-0) + 3-(9-fluoro-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)-4-imidazo[1,2-a]pyridin-3-yl-pyrrole-2,5-dione hydrochloride (603272-51-1) → LY2090314 (603288-22-8)

Guidance literature:

With triethylamine; In methanol; at 20 ℃; for 3h;

DOI:10.1021/jm049768a

Reference yield: 45.0%

piperidine carbamoyl chloride (13939-69-0) + 3-(9-fluoro-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)-4-imidazo[1,2-a]pyridin-3-yl-pyrrole-2,5-dione → LY2090314 (603288-22-8)

Guidance literature:

With triethylamine; In methanol; at 20 ℃;

upstream raw materials:

piperidine carbamoyl chloride

3-(9-fluoro-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)-4-imidazo[1,2-a]pyridin-3-yl-pyrrole-2,5-dione hydrochloride

2-aminopyridine

2-(imidazo-[1,2-a]pyridin-3-yl)acetamide

Refernces

• 1、 -. "POTENTIATION OF CANCER CHEMOTHERAPY". Paragraph 0048. . Retrieved 2015/12/19.
• 2、 Engler, Thomas A.,Henry, James R.,Malhotra, Sushant,Cunningham, Brian,Furness, Kelly,Brozinick, Joseph,Burkholder, Timothy P.,Clay, Michael P.,Clayton, Joshua,Diefenbacher, Clive,Hawkins, Eric,Iversen, Philip W.,Li, Yihong,Lindstrom, Terry D.,Marquart, Angela L.,McLean, Johnathan,Mendel, David,Misener, Elizabeth,Briere, Daniel,O'Toole, John C.,Porter, Warren J.,Queener, Steven,Reel, Jon K.,Owens, Rebecca A.,Brier, Richard A.,Eessalu, Thomas E.,Wagner, Jill R.,Campbell, Robert M.,Vaughn, Renee. "Substituted 3-imidazo[1,2-a]pyridin-3-yl-4-(1,2,3,4-tetrahydro-[1,4] diazepino-[6,7,1-hi]indol-7-yl)pyrrole-2,5-diones as highly selective and potent inhibitors of glycogen synthase kinase-3". . p. 3934 - 3937. Retrieved 2007/10/03.