251540-53-1

Basic information

• Product Name: 2-tert-Butyl-1,3,4-oxadiazole
• Synonyms: 2-TERT-BUTYL-1,3,4-OXADIAZOLE;1,3,4-OXADIAZOLE, 2-(1,1-DIMETHYLETHYL)-;(S)-tert-butyl 2-amino-1-cyclohexylethylcarbamate
• CAS NO: 251540-53-1
• Molecular Formula: C6H10N2O
• Molecular Weight: 126.16
• Mol File: 251540-53-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 168.4 °C at 760 mmHg
• Flash Point: 49.9 °C
• Appearance: /
• Density: 1.006 g/cm³
• Vapor Pressure: 2.15mmHg at 25°C
• Refractive Index: 1.441
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-tert-Butyl-1,3,4-oxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-tert-Butyl-1,3,4-oxadiazole(251540-53-1)
• EPA Substance Registry System: 2-tert-Butyl-1,3,4-oxadiazole(251540-53-1)

Safety Data

• Hazardous Substances Data: 251540-53-1(Hazardous Substances Data)

Usage

Description

2-tert-Butyl-1,3,4-oxadiazole is an organic compound characterized by its five-membered heterocyclic ring structure, which includes three nitrogen atoms and one oxygen atom. It is a versatile intermediate in the synthesis of various pharmaceuticals and chemical compounds due to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
2-tert-Butyl-1,3,4-oxadiazole is used as an intermediate for the preparation of orally active nonpeptidic inhibitors of human neutrophil elastase. These inhibitors play a crucial role in treating diseases associated with the uncontrolled activity of neutrophil elastase, such as chronic obstructive pulmonary disease (COPD) and emphysema.
Additionally, 2-tert-Butyl-1,3,4-oxadiazole is used in the synthesis of Oxadiazolyl ketones, which are potent inhibitors of Dipeptidyl peptidase IV (DPPIV). DPPIV inhibitors have significant applications in the treatment of type 2 diabetes and other metabolic disorders by regulating the levels of glucagon-like peptide-1 (GLP-1), a hormone that helps in glucose homeostasis.

InChI:InChI=1/C6H10N2O/c1-6(2,3)5-8-7-4-9-5/h4H,1-3H3

Upstream product

• 42826-42-6 pivalohydrazide 
• 149-73-5 trimethyl orthoformate 
• 598-98-1 Methyl pivalate 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 122-51-0 orthoformic acid triethyl ester 
• 75-98-9 Trimethylacetic acid 

Downstream Products

• 337969-31-0 N-[(1S)-2-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(methylethyl)-2-oxoethyl]-2-{6-oxo-2-phenyl-5-[(phenylmethoxy)carbonylamino]hydropyrimidinyl}acetamide 
• 337969-42-3 N-[(1S)-2-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-2-hydroxy-1-(methylethyl)ethyl]-2-(6-phenyl-2-pyridyloxy)acetamide 
• 251958-51-7 N-{1-[(5-tert-butyl-[1,3,4]oxadiazol-2-yl)-hydroxy-methyl]-2-methyl-propyl}-2-[2-(4-fluoro-phenyl)-6-oxo-6H-pyrimidin-1-yl]-acetamide 
• 1025890-17-8 N-{1-[(5-tert-butyl-[1,3,4]oxadiazol-2-yl)-hydroxy-methyl]-2-methyl-propyl}-2-[5-(4-chloro-phenyl)-2-oxo-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-acetamide 
• 293329-65-4 N-[2-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(methylethyl)-2-oxoethyl]-2-{6-oxo-2-phenyl-5-[(phenylmethoxy)carbamido]hydropyrimidinyl}acetamide 
• 337969-29-6 N-[(1S)-2-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-2-hydroxy-1-(methylethyl)ethyl]-2-{6-oxo-2-phenyl-5-[(phenylmethoxy)carbonylamino]hydropyrimidinyl}acetamide 
• 1027970-83-7 [1-({1-[(5-tert-butyl-[1,3,4]oxadiazol-2-yl)-hydroxy-methyl]-2-methyl-propylcarbamoyl}-methyl)-6-oxo-2-pyridin-3-yl-1,6-dihydro-pyrimidin-5-yl]-carbamic acid benzyl ester 
• 1027061-73-9 (1-{[1-(5-tert-butyl-[1,3,4]oxadiazole-2-carbonyl)-2-methyl-propylcarbamoyl]-methyl}-6-oxo-2-pyridin-3-yl-1,6-dihydro-pyrimidin-5-yl)-carbamic acid benzyl ester 
• 208847-72-7 [1-({1-[(5-tert-butyl-[1,3,4]oxadiazol-2-yl)-hydroxy-methyl]-2-methyl-propylcarbamoyl}-methyl)-2-(4-fluoro-phenyl)-6-oxo-1,6-dihydro-pyrimidin-5-yl]-carbamic acid benzyl ester 
• 208847-82-9 [1-{[1-(5-tert-butyl-[1,3,4]oxadiazole-2-carbonyl)-2-methyl-propylcarbamoyl]-methyl}-2-(4-fluoro-phenyl)-6-oxo-1,6-dihydro-pyrimidin-5-yl]-carbamic acid benzyl ester 
• 337969-53-6 (2S)-1-{[1-(triphenylmethyl)imidazol-4-yl]carbonyl}-indolin-2-yl-N-[(1S)-2-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-2-hydroxy-1-(methylethyl)ethyl]carboxamide 
• 337969-55-8 (2S)-1-{[1-(triphenylmethyl)imidazol-4-yl]carbonyl}-indolin-2-yl-N-[(1S)-2-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(methylethyl)-2-oxoethyl]carboxamide 
• 337969-54-7 (2S)-1-[1-(triphenylmethyl)imidazol-4-yl]carbonyl-3-(1,2,3,4-tetrahydroisoquinolyl)-N-[(1S)-2-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-2-hydroxy-1-(methylethyl)ethyl]carboxamide 
• 337969-56-9 (2S)-1-{[1-(triphenylmethyl)imidazol-4-yl]carbonyl}-3-(1,2,3,4-tetrahydroisoquinolyl)-N-[(1S)-2-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(methylethyl)-2-oxoethyl]carboxamide 

Relevant articles and documents

Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)?H Bonds

The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2)?H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)?H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α-chiral alkylated azoles, such as 1,3,4-oxadiazoles, oxazoles, and benzo[d]oxazoles as well as 1,3,4-triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp2)?H bond and the involvement of alkyl radical species under the reaction conditions.

Tri-peptide Inhibitors of Serine Elastases

The present invention provides compounds of formula (I): where X is R1—(CR3R4)nOC(O)—; R1—(CR3R4)nC(O)—; R1—C(O)NH(CR3R4)nOC(O)—; R1—C(O)NH(CR3R4)nC(O)—; R1—C(O)(CR3R4)nOC(O)—; or R1—C(O)(CR3R4)nC(O)—; where R1 is optionally substituted C5-10 aryl or heteroaryl; OH or NH2; where R3 and R4 are independently H or methyl; and n is 0 to 6; and Y is —CF3 or one of: where R2 is C1-8 alkyl optionally substituted with halo or —OH; —(CR6R7)p—C5-6 aryl optionally substituted with halo, —OH, C1-8 alkyl, C1-8 haloalkyl, —(CH2)mC(O)NH2 or —(CH2)mOCH3; where R6 and R7 are independently H or methyl; m is 0 to 4, and p is 0 or 1 or a pharmaceutically acceptable salt, ester, metabolite or prodrug thereof

Keto-1,3,4-oxadiazoles as cathepsin K inhibitors

We have prepared a series of cathepsin K inhibitors bearing the keto-1,3,4-oxadiazole warhead capable of forming a hemithioketal complex with the target enzyme. By modifying binding moieties at the P1, P2, and prime side positions of the inhibitors, we have achieved selectivity over cathepsins B, L, and S, and have achieved sub-nanomolar potency against cathepsin K. This series thus represents a promising chemotype that could be used in diseases implicated by imbalances in cathepsin K activity such as osteoporosis.