N-(4-(1-Cyanocyclopentyl)phenyl)-2-((pyridin-4-ylmethyl)amino)nicotinamide

Base Information

• Chemical Name: N-(4-(1-Cyanocyclopentyl)phenyl)-2-((pyridin-4-ylmethyl)amino)nicotinamide
• CAS No.: 811803-05-1
• Molecular Formula: C₂₄H₂₃N₅O
• Molecular Weight: 397.48
• UNII: 5S371K6132
• ChEMBL ID: CHEMBL3186534
• DSSTox Substance ID: DTXSID601024366
• Metabolomics Workbench ID: 155081
• NCI Thesaurus Code: C152237
• Nikkaji Number: J2.963.171I
• Pharos Ligand ID: 3KUD3KH15ADW,7797KZ99NH6L
• Wikidata: Q27262801
• Wikipedia: Apatinib
• Mol file: 811803-05-1.mol

Synonyms:apatinib;apatinib mesylate;rivoceranib;rivoceranib mesylate;YN-968D1;YN968D1

Chemical Property of N-(4-(1-Cyanocyclopentyl)phenyl)-2-((pyridin-4-ylmethyl)amino)nicotinamide

Chemical Property:

• Boiling Point: 578.2±50.0 °C(Predicted)
• PKA: 11.93±0.70(Predicted)
• PSA: 90.70000
• Density: 1.27
• LogP: 4.82238
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 397.19026037
• Heavy Atom Count: 30
• Complexity: 608

Purity/Quality:

99% ^*data from raw suppliers

Apatinib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C1)(C#N)C2=CC=C(C=C2)NC(=O)C3=C(N=CC=C3)NCC4=CC=NC=C4
• Recent ClinicalTrials: Efficacy and Safety of Maintenance Apatinib Combined With Pemetrexed in Advanced Non-squamous Non-small Cell Lung Cancer Patients
• Description: Apatinib mesylate, discovered by Advenchen Laboratories (United States of America, USA) and co-developed by Jiangsu Hengrui Medicine Co. Ltd (China), was approved by the Chinese Food and Drug Administration (CFDA) in October 2014 for the treatment of metastatic gastric carcinoma. Apatinib mesylate is an oral tyrosine kinase inhibitor that selectively inhibits the vascular endothelial growth factor receptor 2 (VEGFR2), which prevents new blood vessel formation selectively in tumor tissue. Apatinib has shown inhibition of the VEGF signaling pathway with an IC50 value of 1 nM for VEGFR-2 in in vitro enzyme experiments. A multicenter phase II study of apatinib is underway with patients in non-triple-negative metastatic breast cancer trials. Non-clinical studies concluded that apatinib may reverse the ATP-binding cassette subfamily B member 1 and subfamily G member 2 (ABCB1- and ABCG2, respectively)-mediated multidrug resistance which allows cancer cells to circumvent certain conventional antineoplastic drugs, suggesting that apatinib could be effective as a combination therapy. Apatinib is a tyrosine kinase inhibitor that potently suppresses the kinase activity of vascular endothelial growth factor 2 (VEGFR2; IC50 = 1 nM). It is less effective against c-kit (IC50 = 429 nM), Ret (IC50 = 13 nM), and c-src (IC50 = 53 nM) and does not inhibit EGFR, Her-2, or FGFR1 (IC50s = >10 μM). Apatinib has been shown to inhibit the proliferation, migration, and tube formation of human umbilical vein endothelial cells stimulated by fetal bovine serum and, either alone, or in combination with chemotherapeutic agents, prevented the growth of several established human tumor xenograft models.
• Uses: Apatinib (YN968D1) is a small-molecule selective multitargeted tyrosine kinase inhibitor with an IC50 of 2.43 nM for the inhibition of VEGFR2.

Technology Process of N-(4-(1-Cyanocyclopentyl)phenyl)-2-((pyridin-4-ylmethyl)amino)nicotinamide

There total 30 articles about N-(4-(1-Cyanocyclopentyl)phenyl)-2-((pyridin-4-ylmethyl)amino)nicotinamide 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: 92.2%

methyl 2-[(pyridin-4-ylmethyl)amino]-3-pyridinecarboxylate + 1-(4-aminophenyl)cyclopentane-1-carbonitrile (115279-73-7) → N-[4-(1-cyanocyclopentyl)phenyl][2-[(4-pyridylmethyl)amino](3-pyridyl)]carboxamide (1275609-09-0,811803-05-1)

Guidance literature:

With copper(l) chloride; In N,N-dimethyl-formamide; at 95 - 105 ℃; for 5h; Temperature;

Reference yield: 92.1%

2-chloro-2-propenal (683-51-2) + N-(4-pyridyl)methyl-N'-4-(1-cyanocyclopentyl)phenylmalonamide → N-[4-(1-cyanocyclopentyl)phenyl][2-[(4-pyridylmethyl)amino](3-pyridyl)]carboxamide (1275609-09-0,811803-05-1)

Guidance literature:

With ammonia; In methanol; ethanol; at 60 - 70 ℃; for 5h; Reagent/catalyst; Solvent;

Reference yield: 91.2%

ethyl 2-[(pyridin-4-ylmethyl)amino]-3-pyridinecarboxylate (1035055-46-9) + 1-(4-aminophenyl)cyclopentane-1-carbonitrile (115279-73-7) → N-[4-(1-cyanocyclopentyl)phenyl][2-[(4-pyridylmethyl)amino](3-pyridyl)]carboxamide (1275609-09-0,811803-05-1)

Guidance literature:

With dmap; In toluene; at 95 - 115 ℃; for 7h;

upstream raw materials:

1-(4-aminophenyl)cyclopentane-1-carbonitrile

4-(aminomethyl)pyridine

N-[4-(1-cyanocyclopentyl)phenyl][2-chloro(3-pyridyl)]carboxamide

phenylacetonitrile