Dutogliptin

Base Information

• Chemical Name: Dutogliptin
• CAS No.: 852329-66-9
• Molecular Formula: C10H20BN3O3
• Molecular Weight: 241.098
• UNII: 38EAO245ZX
• ChEMBL ID: CHEMBL4296719
• DSSTox Substance ID: DTXSID301005713
• Metabolomics Workbench ID: 152833
• NCI Thesaurus Code: C87492
• Nikkaji Number: J3.333.210F
• Pharos Ligand ID: 7UYXC9GAJUDR
• Mol file: 852329-66-9.mol

Synonyms:dutogliptin

Chemical Property of Dutogliptin

Chemical Property:

• Boiling Point: 494.6±55.0 °C(Predicted)
• PKA: 9.71±0.20(Predicted)
• PSA: 84.83000
• Density: 1.24±0.1 g/cm3(Predicted)
• LogP: -0.98160
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 241.1597717
• Heavy Atom Count: 17
• Complexity: 278

Purity/Quality:

99% ^*data from raw suppliers

Dutogliptin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1CCCN1C(=O)CNC2CCNC2)(O)O
• Isomeric SMILES: B([C@@H]1CCCN1C(=O)CN[C@@H]2CCNC2)(O)O
• Recent ClinicalTrials: Dutogliptin in Co-administration With Filgrastim in Early Recovery Post-myocardial Infarction
• Recent EU Clinical Trials: A Phase III, Multicenter, Double-blind, Active-Controlled, 52-Week Extension Study to Evaluate the Safety and Efficacy of Dutogliptin in Patients With Type 2 Diabetes Mellitus Receiving Background Treatment With Glimepiride Alone or in Combination With Metformin or With Pioglitazone Alone

Technology Process of Dutogliptin

There total 4 articles about Dutogliptin 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:

(2R)-1-{2-[(3R)-pyrrolidinylamino]-acetyl}-pyrrolidine-2-boronic acid (1S,2S,3R,5S)-pinanediol ester (923566-03-4) → Dutogliptin (852329-66-9)

Guidance literature:

With hydrogenchloride; phenylboronic acid; In water; for 24h; pH=2;

Reference yield:

3-(R)-(benzyloxycarbonyl-carboxymethyl-amino)-pyrrolidine-1-carboxylic acid benzyl ester (1056211-06-3,1184179-07-4) → Dutogliptin (852329-66-9)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 25 °C

2: hydrogen; 0.5% Pd/C / methanol / 5 - 30 °C / 2250.23 - 6750.68 Torr

3: hydrogenchloride; phenylboronic acid / water / 24 h / pH 2

With hydrogenchloride; 0.5% Pd/C; hydrogen; N-ethyl-N,N-diisopropylamine; phenylboronic acid; In methanol; dichloromethane; water;

Reference yield:

(R)-3-(Benzyloxycarbonyl-{2-oxo-2-[(R)-2-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-pyrrolidin-1-yl]-ethyl}-amino)-pyrrolidine-1-carboxylic acid benzyl ester → Dutogliptin (852329-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; 0.5% Pd/C / methanol / 5 - 30 °C / 2250.23 - 6750.68 Torr

2: hydrogenchloride; phenylboronic acid / water / 24 h / pH 2

With hydrogenchloride; 0.5% Pd/C; hydrogen; phenylboronic acid; In methanol; water;

upstream raw materials:

3-(R)-(benzyloxycarbonyl-carboxymethyl-amino)-pyrrolidine-1-carboxylic acid benzyl ester

(2R)-1-{2-[(3R)-pyrrolidinylamino]-acetyl}-pyrrolidine-2-boronic acid (1S,2S,3R,5S)-pinanediol ester

Downstream raw materials:

dutogliptin-L-tartrate

Refernces

• 1、 -. "SOLID CITRATE AND TARTRATE SALTS OF DPP-IV INHIBITORS". Page/Page column 30-33. . Retrieved 2008/06/13.