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

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

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 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 122-51-0 orthoformic acid triethyl ester 
• 75-98-9 Trimethylacetic acid 
• 598-98-1 Methyl pivalate 

Downstream Products

• 851028-87-0 tert-butyl-(2S,4S)-2-[(5-tert-butyl-1,3,4-oxadiazol-2-yl)carbonyl]-4-fluoropyrrolidine-1-carboxylate 
• 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 
• 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 
• 337969-55-8 (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 
• 337969-53-6 (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 
• 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 
• 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 
• 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 
• 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 
• 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 
• 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 
• 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 
• 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 
• 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 

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.

Transition-metal-free oxidative iodination of 1,3,4-oxadiazoles

Transition-metal-free oxidative iodination of 2-substituted 1,3,4-oxadiazoles was achieved by using sodium iodide as the halide source and Selectfluor as the oxidant. Variously substituted products were obtained in moderate to good yields under operationa

Tri-peptide Inhibitors of Serine Elastases

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Development of a kilogram-scale synthesis of cis-LC15-0133 tartrate, a potent dipeptidyl peptidase IV inhibitor

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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.

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The present invention relates to certain substituted oxadiazole peptoids and nonpeptoids useful as inhibitors of serine proteases, especially human neutophil elastase (HNE). Compounds of the present invention are useful for the treatment or amelioration of symptoms of adult respiratory distress syndrome, septic shock, and multiple organ failure. Processes mediated by HNE are also implicated in conditions such as arthritis, periodontal disease, glomerulonephritis, and cystic fibrosis.

Development of orally active nonpeptidic inhibitors of human neutrophil elastase

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Indole and tetrahydroisoquinoline containing Alpha-keto oxadiazoles as serine protease inhibitors

The present invention relates to certain substituted oxadiazole nonpeptides, which are useful as inhibitors of human neutrophil elastase (HNE) for the treatment of HNE-mediated processes implicated in conditions such as adult respiratory distress syndrome, septic shock and multiple organ failure. A series of studies also have indicated the involvement HNE in myocardial ischemia-reperfusion injury, emphysema. HNE-mediated processes are implicated in other conditions such as arthritis, periodontal disease, glomerulonephritis, dermatitis, psoriasis, cystic fibrosis, chronic bronchitis, atherosclerosis, Alzheimer's disease, organ transplantation, corneal ulcers, and invasion behavior of malignant tumors.

VAL-PRO CONTAINING ALPHA-KETO OXADIAZOLES AS SERINE PROTEASE INHIBITORS

The present invention relates to certain substituted oxadiazole tripeptides, which are useful as inhibitors of human neutrophil elastase (HNE) for the treatment of HNE-mediated processes implicated in conditions such as adult respiratory distress syndrome, septic shock and multiple organ failure. A series of studies also have indicated the involvement HNE in myocardial ischemia-reperfusion injury, emphysema. HNE-mediated processes are implicated in other conditions such as arthritis, periodontal disease, glomerulonephritis, dermatitis, psoriasis, cystic fibrosis, chronic bronchitis, atherosclerosis, Alzheimer's disease, organ transplantation, corneal ulcers, and invasion behavior of malignant tumors.