(2S)-1-(2-((2-((5-Cyano-2-pyridyl)amino)ethyl)amino)acetyl)pyrrolidine-2-carbonitrile

Base Information

• Chemical Name: (2S)-1-(2-((2-((5-Cyano-2-pyridyl)amino)ethyl)amino)acetyl)pyrrolidine-2-carbonitrile
• CAS No.: 247016-69-9
• Molecular Formula: C15H18N6O
• Molecular Weight: 371.26500
• UNII: HCX5M1YIOM
• DSSTox Substance ID: DTXSID70624696
• Nikkaji Number: J1.243.445F
• Wikidata: Q76411441
• Pharos Ligand ID: KCVD3BV9VSH2
• ChEMBL ID: CHEMBL77538
• Mol file: 247016-69-9.mol

Synonyms:1-(((2-((5-cyanopyridin-2-yl)amino)ethyl)amino)acetyl)-2-cyano-(S)-pyrrolidine;NVP-DPP728

Chemical Property of (2S)-1-(2-((2-((5-Cyano-2-pyridyl)amino)ethyl)amino)acetyl)pyrrolidine-2-carbonitrile

Chemical Property:

• Melting Point: 167 °C (approx)
• Boiling Point: 612.1±55.0 °C(Predicted)
• PKA: 7.47±0.20(Predicted)
• PSA: 104.84000
• Density: 0.1 g/cm3
• LogP: 2.47516
• Storage Temp.: Desiccate at RT
• Solubility.: ≥17.75 mg/mL in DMSO with gentle warming; ≥81 mg/mL in EtOH; ≥82 mg/mL in H2O
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 298.15420922
• Heavy Atom Count: 22
• Complexity: 475

Purity/Quality:

99% ，98% ^*data from raw suppliers

NVP DPP 728 dihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)CNCCNC2=NC=C(C=C2)C#N)C#N
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)CNCCNC2=NC=C(C=C2)C#N)C#N
• Uses: NVP DPP 728 Dihydrochloride is a new potent DPP-IV inhibitor class with excellent oral bioavailability and potent antihyperglycemic activity.

Technology Process of (2S)-1-(2-((2-((5-Cyano-2-pyridyl)amino)ethyl)amino)acetyl)pyrrolidine-2-carbonitrile

There total 9 articles about (2S)-1-(2-((2-((5-Cyano-2-pyridyl)amino)ethyl)amino)acetyl)pyrrolidine-2-carbonitrile 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: 80.0%

N-[2-(5-cyano-pyridin-2-ylamino)-ethyl]-N-[2-(2-cyano-pyrrolidin-1-yl)-2-oxo-ethyl]-2,2,2-trifluoro-acetamide → (S)-1-{2-[(5-cyanopyridin-2-yl)amino]ethyl-aminoacetyl}-2-cyano-pyrrolidine (247016-69-9)

Guidance literature:

With ammonium hydroxide; In dichloromethane; for 3h;

DOI:10.1016/S0040-4020(02)00536-7

Reference yield: 75.0%

6-{3-[2-((2S)-cyanopyrrolidin-1-yl)-2-oxoethyl]imidazolidin-1-yl}nicotinonitrile → (S)-1-{2-[(5-cyanopyridin-2-yl)amino]ethyl-aminoacetyl}-2-cyano-pyrrolidine (247016-69-9)

Guidance literature:

With 3-(4-(hydrazinosulfonyl)phenylpropionyl AM resin; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(02)00536-7

Reference yield: 34.0%

(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile (207557-35-5) + 6-[(2-aminoethyl)amino]pyridine-3-carbonitrile (202460-48-8) → (S)-1-{2-[(5-cyanopyridin-2-yl)amino]ethyl-aminoacetyl}-2-cyano-pyrrolidine (247016-69-9)

Guidance literature:

In tetrahydrofuran; for 2h; cooling;

DOI:10.1021/jm025522z

upstream raw materials:

(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile

6-[(2-aminoethyl)amino]pyridine-3-carbonitrile

(S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide

L-prolinamide

Refernces

• 1、 Villhauer, Edwin B.,Brinkman, John A.,Naderi, Goli B.,Burkey, Bryan F.,Dunning, Beth E.,Prasad, Kapa,Mangold, Bonnie L.,Russell, Mary E.,Hughes, Thomas E.. "1-[[(3-Hydroxy-1-adamantyl)amino]acetyl]-2-cyano-(S)-pyrrolidine: A potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties". . p. 2774 - 2789. Retrieved 2007/10/03.