1104599-71-4

Basic information

• Product Name: 3-((1S,3R)-3-(4-(4-fluorophenyl)-1H-imidazol-2-yl)-1-(1-methyl-1H-pyrazol-4-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)-5-methyl-1,2,4-oxadiazole
• CAS NO: 1104599-71-4
• Molecular Weight: 494.531
• Mol File: 1104599-71-4.mol

Chemical Properties

• CAS DataBase Reference: 3-((1S,3R)-3-(4-(4-fluorophenyl)-1H-imidazol-2-yl)-1-(1-methyl-1H-pyrazol-4-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)-5-methyl-1,2,4-oxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-((1S,3R)-3-(4-(4-fluorophenyl)-1H-imidazol-2-yl)-1-(1-methyl-1H-pyrazol-4-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)-5-methyl-1,2,4-oxadiazole(1104599-71-4)
• EPA Substance Registry System: 3-((1S,3R)-3-(4-(4-fluorophenyl)-1H-imidazol-2-yl)-1-(1-methyl-1H-pyrazol-4-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)-5-methyl-1,2,4-oxadiazole(1104599-71-4)

Safety Data

• Hazardous Substances Data: 1104599-71-4(Hazardous Substances Data)

Upstream product

• 1104240-73-4 (5-methyl-1,2,4-oxadiazol-3-yl)(1-methyl-1H-pyrazol-4-yl)methanone 
• 1104606-50-9 (R)-1-(4-(4-fluorophenyl)-1H-imidazol-2-yl)-2-(1H-indol-3-yl)-ethanamine hydrochloride 
• 1104606-06-5 (R)-tert-butyl (1-(4-(4-fluorophenyl)-1H-imidazol-2-yl)-2-(1H-indol-3-yl)ethyl)carbamate 
• 5241-64-5 Boc-D-Trp-OH 
• 403-29-2 2-bromo-4'-fluoroacetophenone 
• 1411994-50-7 C₂₄H₂₅FN₂O₅ 

Relevant articles and documents

Route development and multikilogram GMP delivery of a somatostatin receptor antagonist

Route development and demonstration on multikilogram scale for the first GMP delivery of MK-4256 are described. Key aspects of the convergent route include a regioselective green iodination, one-pot oxadiazole synthesis, and an efficient ketone Pictet-Spengler reaction with diastereomeric upgrade via crystallization to afford 6 kg of API. A recycle procedure augmented the yield of desired diastereomer in the Pictet-Spengler reaction from a mixture of diastereomers heavily enriched in the undesired diastereomer.

The discovery of MK-4256, a potent SSTR3 antagonist as a potential treatment of type 2 diabetes

A structure-activity relationship study of the imidazolyl-β- tetrahydrocarboline series identified MK-4256 as a potent, selective SSTR3 antagonist, which demonstrated superior efficacy in a mouse oGTT model. MK-4256 reduced glucose excursion in a dose-dependent fashion with maximal efficacy achieved at doses as low as 0.03 mg/kg po. As compared with glipizide, MK-4256 showed a minimal hypoglycemia risk in mice.