Gosogliptin

Base Information

• Chemical Name: Gosogliptin
• CAS No.: 869490-23-3
• Molecular Formula: C₁₇H₂₄F₂N₆O
• Molecular Weight: 366.414
• UNII: GI718UO477
• ChEMBL ID: CHEMBL515387
• DSSTox Substance ID: DTXSID601007213
• Metabolomics Workbench ID: 151519
• NCI Thesaurus Code: C90616
• Pharos Ligand ID: XBJUQSRK36V7
• Wikidata: Q27077831
• Wikipedia: Gosogliptin
• Mol file: 869490-23-3.mol

Synonyms:gosogliptin;PF-00734200;PF-734,200;PF-734200

Chemical Property of Gosogliptin

Chemical Property:

• Boiling Point: 562.3±60.0 °C(Predicted)
• PKA: 8.95±0.10(Predicted)
• PSA: 64.60000
• Density: 1.36
• LogP: 0.46630
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 366.19796573
• Heavy Atom Count: 26
• Complexity: 508

Purity/Quality:

99% ^*data from raw suppliers

Gosogliptin 99.27% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC1(F)F)C(=O)C2CC(CN2)N3CCN(CC3)C4=NC=CC=N4
• Isomeric SMILES: C1CN(CC1(F)F)C(=O)[C@@H]2C[C@@H](CN2)N3CCN(CC3)C4=NC=CC=N4
• Recent ClinicalTrials: Efficacy and Safety of Gosogliptin as Monotherapy and in Combination With Metformin vs. Vildagliptin as Monotherapy and in Combination With Metformin in Drug-naive Type 2 Diabetic Patients.
• Recent EU Clinical Trials: A PHASE 2, RANDOMIZED, DOUBLE-BLIND, PLACEBO-CONTROLLED, PARALLEL GROUP STUDY TO EVALUATE THE EFFICACY AND SAFETY OF 12-WEEK ADMINISTRATION OF PF-00734200 TO SUBJECTS WITH TYPE 2 DIABETES MELLITUS AND INSUFFICIENT GLYCEMIC CONTROL ON METFORMIN TREATMENT
• Uses: Gosogliptin is used as a treatment for type 2 diabetes.

Technology Process of Gosogliptin

There total 7 articles about Gosogliptin 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: 83.0%

tert-butyl (2S,4S)-2-(3,3-difluoropyrrolidine-1-carbonyl)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidine-1,2-dicarboxylate → (3,3-difluoropyrrolidin-1-yl)-((2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidin-2-yl)methanone (869490-23-3)

Guidance literature:

tert-butyl (2S,4S)-2-(3,3-difluoropyrrolidine-1-carbonyl)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidine-1,2-dicarboxylate; With hydrogenchloride; In water; at 20 ℃; for 4h;

With sodium hydroxide; In water; at 5 - 20 ℃; pH=10 - 11;

DOI:10.1021/op200309z

Reference yield:

N-(2-pyridinyl)piperazine (20980-22-7) → (3,3-difluoropyrrolidin-1-yl)-((2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidin-2-yl)methanone (869490-23-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / acetonitrile / 18 h / Reflux

2.1: lithium hydroxide / tetrahydrofuran; water / 4 h / 20 °C

2.2: 0 - 20 °C

3.1: hydrogenchloride / water / 4 h / 20 °C

3.2: 5 - 20 °C / pH 10 - 11

With hydrogenchloride; potassium carbonate; lithium hydroxide; In tetrahydrofuran; water; acetonitrile;

DOI:10.1021/op200309z

Reference yield:

1-tert-butyl 2-methyl (2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidine-1,2-dicarboxylate (1361054-82-1) → (3,3-difluoropyrrolidin-1-yl)-((2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidin-2-yl)methanone (869490-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hydroxide / tetrahydrofuran; water / 4 h / 20 °C

1.2: 0 - 20 °C

2.1: hydrogenchloride / water / 4 h / 20 °C

2.2: 5 - 20 °C / pH 10 - 11

With hydrogenchloride; lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1021/op200309z

upstream raw materials:

1-tert-butyl 2-methyl (2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidine-1,2-dicarboxylate

C₁₇H₂₃NO₇S

N-(2-pyridinyl)piperazine

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Refernces

• 1、 -. "Therapeutic compounds". Page/Page column 18-19. . Retrieved 2008/06/13.