Carmegliptin

Base Information

• Chemical Name: Carmegliptin
• CAS No.: 813452-18-5
• Molecular Formula: C₂₀H₂₈FN₃O₃
• Molecular Weight: 377.459
• UNII: 9Z723VGH7J
• ChEMBL ID: CHEMBL591118
• DSSTox Substance ID: DTXSID401001938
• Metabolomics Workbench ID: 153287
• NCI Thesaurus Code: C81698
• Pharos Ligand ID: X1FRWP5UJBYP
• Mol file: 813452-18-5.mol

Synonyms:carmegliptin

Chemical Property of Carmegliptin

Chemical Property:

• PSA: 68.03000
• LogP: 2.09670
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 377.21146993
• Heavy Atom Count: 27
• Complexity: 551

Purity/Quality:

97% ^*data from raw suppliers

CARMEGLIPTIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C3CC(C(CN3CCC2=C1)N4CC(CC4=O)CF)N)OC
• Isomeric SMILES: COC1=C(C=C2[C@@H]3C[C@@H]([C@H](CN3CCC2=C1)N4C[C@H](CC4=O)CF)N)OC
• Recent ClinicalTrials: A Study of Dipeptidyl-peptidase IV (DPP-IV) RO4876904 in Patients With Type 2 Diabetes.
• Recent EU Clinical Trials: Multicenter, double-blind, randomized, placebo-controlled, dose ranging phase 2 study to investigate efficacy, safety, tolerability and pharmacokinetics of the DPP-IV inhibitor RO4876904 in patients with type 2 diabetes

Technology Process of Carmegliptin

There total 6 articles about Carmegliptin 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: 91.0%

(2S,3S,11bS)-[3-((4S)-4-(fluoromethyl)-2-oxo-pyrrolidin-1-yl)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl]-carbamic acid tert-butyl ester (813452-16-3) → (S)-1-((2S,3S,11bS)-2-amino-9, 10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-3-yl)-4-fluoromethyl-pyrrolidin-2-one (813452-18-5)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane;

DOI:10.1016/j.bmcl.2009.12.024

Reference yield:

[(S,S,S)-3-((R)-4-fluoromethyl-2-oxo-pyrrolidin-1-yl)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl]-carbamic acid tert-butyl ester → (R)-1-((2S,3S,11bS)-2-amino-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-3-yl)-4-fluoromethyl-pyrrolidin-2-one (813452-18-5)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane;

DOI:10.1016/j.bmcl.2009.12.024

Reference yield:

1-((RS,RS,RS)-2-amino-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-3-yl)-4-fluoromethyl-pyrrolidin-2-one (813452-18-5) → (RS,RS,RS,RS)-1-(2-amino-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-3-yl)-4-fluoromethyl-pyrrolidin-2-one (813452-18-5) + (SR)-1-((RS,RS,RS)-2-amino-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-3-yl)-4-fluoromethyl-pyrrolidin-2-one (813452-18-5)

Guidance literature:

Purification / work up;

upstream raw materials:

(2S,3S,11bS)-[3-((4S)-4-(fluoromethyl)-2-oxo-pyrrolidin-1-yl)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl]-carbamic acid tert-butyl ester

Refernces

• 1、 -. "Pyrido [2,1-a] isoquinoline derivatives". Page 21. . Retrieved 2010/02/09.