39968-33-7

Basic information

• Product Name: HOAt
• Synonyms: 3H-1,2,3-TRIAZOLO[4,5-B]PYRIDINE, 3-HYDROXY-;3H-[1,2,3]-TRIAZOLO[4,5-B]PYRIDIN-3-OL;7-AZA-1-HYDROXYBENZOTRIAZOLE;HOAT;1-HYDROXY-7-AZABENZOTRIAZOLE 0.5 TO &;1-HYDROXY-7-AZABENZOTRIAZOLE SOLUTION, 0.5M IN DMF;HOAT [1-HYDROXY-7-AZABENZOTRIAZOLE];1-Hydroxy-7-Azabenzotriazole99%Puriss
• CAS NO: 39968-33-7
• Molecular Formula: C₅H₄N₄O
• Molecular Weight: 136.11
• EINECS: 609-760-3
• Product Categories: Peptide coupling agents;Heterocycles;PROTECTED AMINO ACID & PEPTIDES;Peptide Coupling Reagents;Heterocyclic Compounds;Peptide;Bases & Related Reagents;Nucleotides;peptides
• Mol File: 39968-33-7.mol

Chemical Properties

• Melting Point: 213-216°C
• Boiling Point: 250.36°C (rough estimate)
• Flash Point: 213-216°C
• Appearance: Clear, colorless liquid
• Density: 0.973 g/mL at 20 °C
• Vapor Pressure: 3.25E-06mmHg at 25°C
• Refractive Index: n20/D 1.441
• Storage Temp.: Store at RT.
• PKA: 5.85±0.58(Predicted)
• CAS DataBase Reference: HOAt(CAS DataBase Reference)
• NIST Chemistry Reference: HOAt(39968-33-7)
• EPA Substance Registry System: HOAt(39968-33-7)

Safety Data

• Hazard Codes: T,Xi,F,Xn,E
• Statements: 61-20/21-36-5-36/37/38-11-41-37/38-22-2-36/37
• Safety Statements: 53-45-37/39-26-16-39-35-36-36/37-28-15
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 1
• HazardClass: IRRITANT
• PackingGroup: Ⅱ
• Hazardous Substances Data: 39968-33-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10H

Upstream product

• 20265-37-6 3-methoxy-2-nitropyridine 
• 61822-85-3 3-methoxy-3H-[1,2,3]triazolo[4,5-b]pyridine 
• 110-91-8 morpholine 
• 15128-82-2 3-hydroxy-2-nitropyridine 
• 17407-55-5 (S)-2-Hydroxy-3-methylbutanoic acid 
• 200731-31-3 HATU 
• 4530-20-5 BOC-glycine 
• 214360-73-3 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline 
• 110-89-4 piperidine 
• 54231-32-2 3-chloro-2-nitropyridine 
• 77897-23-5 (3S)-3-benzylmorpholine 
• 1551373-17-1 C₈H₇BrN₄O₂ 
• 930-69-8 sodium thiophenolate 

Downstream Products

• 220903-36-6 3-(2-(1-Z-pentenyl)phenyl)-E-acrylic acid hydroxyazo benzotriazolyl ester 
• 154561-21-4 Z-Aib-OAt 
• 370104-37-3 3-[benzo[1,3]dioxol-5-yl-([1,2,3]triazolo[4,5-b]pyridin-3-yloxycarbonyl)-methyl]-1-methyl-1H-indole-6-carboxylic acid benzyl ester 
• 540483-09-8 1-diphenoxyphosphinyloxy-7-azabenzotriazole 

Relevant articles and documents

Development of a Stereoselective and Scalable Synthesis for the Potent Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitor, BMT-297376; N-((R)-1-((cis)-4-(3-(Difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl)propyl)-6-methoxynicotinamide

The current work describes a stereoselective and scalable route to N-((R)-1-((cis)-4-(3-(difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl)propyl)-6-methoxynicotinamide (1) from readily available 1,4-dioxaspiro[4.5]decan-8-one. The developed process encompasses an efficient 1,4-trans-selective synthesis of (trans)-4-(3-(difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl methanesulfonate as the key intermediate and the use of Ellman sulfinamine methodology to install an alkyl amine in a stereoselective manner. Various synthetic routes were screened to accomplish a stereoselective and scalable protocol to access the title compound (1). This advancement enabled a competent route to the title compound in an enantioselective, safe, cost-effective, and scalable manner.

Concerted amidation of activated esters: Reaction path and origins of selectivity in the kinetic resolution of cyclic amines via N-heterocyclic carbenes and hydroxamic acid cocatalyzed acyl transfer

The N-heterocyclic carbene and hydroxamic acid cocatalyzed kinetic resolution of cyclic amines generates enantioenriched amines and amides with selectivity factors up to 127. In this report, a quantum mechanical study of the reaction mechanism indicates that the selectivity-determining aminolysis step occurs via a novel concerted pathway in which the hydroxamic acid plays a key role in directing proton transfer from the incoming amine. This modality was found to be general in amide bond formation from a number of activated esters including those generated from HOBt and HOAt, reagents that are broadly used in peptide coupling. For the kinetic resolution, the proposed model accurately predicts the faster reacting enantiomer. A breakdown of the steric and electronic control elements shows that a gearing effect in the transition state is responsible for the observed selectivity.

One-step radiosynthesis of 4-nitrophenyl 2-[18F]fluoropropionate ([18F]NFP); Improved preparation of radiolabeled peptides for PET imaging

The versatile 18F-labeled prosthetic group, 4-nitrophenyl 2-[18F]fluoropropionate ([18F]NFP), was synthesized in a single step in 45 min from 4-nitrophenyl 2-bromopropionate, with a decay corrected radiochemical yield of 26.2% ± 2.2%. Employing this improved synthesis of [18F]NFP, [18F]GalactoRGD - the current 'gold standard' tracer for imaging the expression of αVβ 3 integrin - was prepared with high specific activity in 90 min and 20% decay corrected radiochemical yield from [18F]fluoride. 4-Nitrophenyl 2-[18F]fluoropropionate ([18F]NFP), was synthesized in a single radiochemical step in 45 minutes and 26% d.c. radiochemical yield from 4-nitrophenyl 2-bromopropionate. Employing this improved synthesis of [18F]NFP, [18F]GalactoRGD was prepared with high specific activity in 90 minutes and 20% d.c. radiochemical yield from [18F]fluoride. Copyright

Spectrophotometric determination of pKa's of 1-Hydroxybenzotriazole and oxime derivatives in 95% acetonitrile-water

1-hydroxybenzotriazole derivatives are used with carbodiimide as additives to generate active esters during peptide bond formation. They are also used as additives during the peptide bond formation. Dissociation constants of the 1-hdroxybenzotriazole (HOBt) and its derivatives, 1- hydroxy-6- chlorobenzotriazole, 1-hydroxy-6-trifluoromethylbenzotriazole, 1-hydroxy-6-nitrobenzotriazole were determined spectrophotometrically in 95% acetonitrile-water. In addition, 7-aza-1- hydroxybenzotriazole (7-HOAt) and 4-aza-1-hydroxybenzotriazole (4-HOAt) were also studied. Recently, oxyma was reported as a good replacement for the benzotriazole derivatives. As alcoholic components of active esters, the oximes seem to be good leaving groups. Therefore it was expected, that the strongly acidic and nucleophilic oximes, which possess electron-withdrawing groups in the molecule, are suitable as additives during the peptide bond formation. The dissociation constant of some oximes,such as diethyl 2-(hydroxyimino)malonate, ethyl 2-cyano-2-(hydroxyimino) acetate (oxyma), hydroxycarbonimidoyl dicyanide and N-hydroxypicolinimidoyl cyanide in 95% acetonitrile-water are reported.

Synthesis and aminolysis of N,N-diethyl carbamic ester of HOBt derivatives

The reaction of N,N-diethyl carbamates of 1H-[1,2,3]triazolo[4,5-b]pyridin- 1-ol (4-HOAt) 7, 3H-[1,2,3]triazolo[4,5- b]pyridin-3-ol (7-HOAt) 8, 1H-benzo[d][1,2,3]triazol-1-ol (HOBt) 9, 6-chloro-1H-benzo[d][1,2,3]triazol-1-ol (Cl- HOBt) 10, 6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-1-ol (CF3 3-HOBt) 11, and 6-nitro-1H-benzo[d][1,2,3]triazol- 1-ol (NO2 2-HOBt) 12 with morpholine and piperidine in CH3CN underwent acyl nucleophilic substitution to give the corresponding carboxamide derivatives. The reactants and products were identified by elemental analysis, IR and NMR. We measured the kinetics of these reactions spectrophotometrically in CH3 3CN at a range of temperatures. The rates of morpholinolysis and piperidinolysis were found to fit the Hammett equation and correlated with s-Hammett values. The values were 1.44 - 1.21 for morpholinolysis and 1.95 - 1.72 for piperidinolysis depending on the temperature. The Bronsted-type plot was linear with a βlg = -0.49 ± 0.02 and -0.67 ± 0.03. The kinetic data and structure-reactivity relationships indicate that the reaction of 9-12 with amines proceeds by a concerted mechanism. The deviation from linearity of the correlation ?H# vs. ?S# and plot of logkpip vs. logkmorph and Bronsted-type correlation indicate that the reactions of amines with carbamates 7 and 8 is attributed to the electronic nature of their leaving groups.

2-BENZIMIDAZOLYL-6-MORPHOLINO-4-PHENYLPYRIMIDINE DERIVATIVES AS PI3K AND MTOR INHIBITORS FOR THE TREATMENT OF PROLIFERATIVE DISORDERS

The invention concerns pyrimidine derivatives of Formula (I), wherein each of p, R1, R2, q, R3, r, R4, X1 and Q1 have any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in a method for producing an anti-proliferative effect in a warm blooded animal such as man.

Synthesis and morpholinolysis of N,N-diethyl carbamate derivatives of 4- HOAt, 7-HOAt and HOBt

N,N-Diethyl carbamates of 1-hydroxy-7-azabenzotriazole (7-HOAt), 1-hydroxy-4-azabenzotriazole (4-HOAt), 1-hydroxybenzotriazole (HOBt), and 1-hydroxypyrrolidine-2,5-dione have been synthesised. The reactivities of these active esters have been determined by studying the kinetics and mechanism of their morpholinolysis in acetonitrile at different temperatures.

Hepatitis C virus inhibitors

The present disclosure is generally directed to antiviral compounds, and more specifically directed to compounds which inhibit the function of the NS3 protease (also referred to herein as “serine protease”) encoded by Hepatitis C virus (HCV), compositions comprising such compounds, and methods for inhibiting the function of the NS3 protease.

Novel stabilized activated derivatives of carbamic acid, their process of preparation and their use for the preparation of ureas

Process for the preparation of stable activated derivatives of carbamic acid, comprising at least one protected amino group and an activated carbamic acid function, from an amino acid derivative in which the amino group is protected. The process includes: a) a step of transformation of the —COOH group of the amino acid derivative into a —CON3 group to obtain an acyl azide; b) a step of transformation of the —CON3 group of the acyl azide into a —NCO group to obtain an isocyanate; c) a step of treating the isocyanate to obtain a stable derivative of carbamic acid.

Comparison of the effects of 5- and 6-HOAt on model peptide coupling reactions relative to the cases for the 4- and 7-isomers

(equation presented) Synthesis of 5- and 6-HOAt has completed the full set of the four HOAt isomers derived from HOBt by insertion of a single nitrogen atom in the benzenoid nucleus. Comparison of the reactivity of all four isomers in model peptide coupling reactions has confirmed the unique character of the 7-isomer in promoting selectivity and maintaining configuration at the reactive carboxylic acid residue.