Omarigliptin (MK-3102)

Base Information

• Chemical Name: Omarigliptin (MK-3102)
• CAS No.: 1226781-44-7
• Molecular Formula: C17H20F2N4O3S
• Molecular Weight: 398.434
• Mol file: 1226781-44-7.mol

Synonyms:mk-3102;

Chemical Property of Omarigliptin (MK-3102)

Chemical Property:

• Boiling Point: 529.4±60.0 °C(Predicted)
• PKA: 9.11±0.60(Predicted)
• PSA: 98.83000
• Density: 1.61±0.1 g/cm3(Predicted)
• LogP: 2.86110
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: insoluble in EtOH; insoluble in H2O; ≥17.15 mg/mL in DMSO

Purity/Quality:

99% up, ^*data from raw suppliers

Omarigliptin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Merck earned its first global approval for omarigliptin in Japan in 2015, and phase III development is ongoing in other countries around the globe for this interesting small molecule DPP-4 inhibitor. Interestingly, while most DPP-4 inhibitors used to treat type 2 DM require daily administration, omarigliptin is a weekly treatment. The process-scale synthesis of omarigliptin has been nicely described in an October 2015 paper from the Merck process group. MK-3102 is a potent, reversible, and competitive inhibitor of dipeptidyl peptidase 4 (DPP-4; IC50 = 1.6 nM; Ki = 0.8 nM). It is selective for DPP-4 over 168 proteases, ion channels, and enzymes with IC50 values greater than 10 μM in all assays. MK-3102 significantly reduces blood glucose levels in a dose-dependent manner in vivo in rats. It also has a long half-life (11 and 22 hours in rat and dog, respectively) making it suitable for once weekly dosing. Clinical trials demonstrate that formulations containing MK-3102 reduce plasma glucose and HbA1c in patients with type 2 diabetes mellitus (T2DM).
• Uses: Omarigliptin is a potent and selective dipeptidyl peptidase 4 (DPP-4) inhibitor to be used as treatment for type 2 diabetes.

Technology Process of Omarigliptin (MK-3102)

There total 67 articles about Omarigliptin (MK-3102) 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: 100.0%

C17H18F2N4O5S → Omarigliptin (1226781-44-7)

Guidance literature:

With acetic acid; zinc; In butan-1-ol; at 30 ℃; Temperature; Solvent;

Reference yield: 89.0%

tert-butyl {(2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate (1226781-87-8) → Omarigliptin (1226781-44-7)

Guidance literature:

tert-butyl {(2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate; With sulfuric acid; In N,N-dimethyl acetamide; water; at 20 ℃; for 18.5h;

With ammonium hydroxide; In N,N-dimethyl acetamide; water; pH=10.2;

DOI:10.1021/jm401992e

Reference yield: 87.1%

C18H20F2N4O4S → Omarigliptin (1226781-44-7)

Guidance literature:

With sodium hypochlorite; sodium hydroxide; zinc(II) chloride; In water; at 0 - 60 ℃; for 6h; Large scale;

upstream raw materials:

tert-butyl {(2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate

2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate

[(2R,3S)-5-methylene-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-yl]carbamic acid tert-butyl ester

N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester