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1-methyl-1-piperidinomethane sulfonate →

1-hydroxybenzotriazole

1-Hydroxybenzotriazole is a versatile reagent used in organic synthesis, particularly in peptide chemistry and enzyme catalysis.
It serves as an activator for carboxylic acids, enabling efficient coupling reactions.
This heterocyclic compound enhances the reactivity and selectivity of various transformations, making it a valuable tool for chemical researchers.
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Most cited protocols related to «1-hydroxybenzotriazole»

Optimized Synthesis of Isotopically Labeled M2TM

Due to the requirements for a large quantity of isotopically labeled peptides and the hydrophobic nature of M2TM, we developed an optimized procedure that delivers crude peptide with >80% purity. Problems encountered in obtaining high-yields and purity included aspartamide formation at residue 44 and slow coupling near the center of the chain. M2TM(22–46) with uniformly ¹³C, ¹⁵N-labeled V27, A30 and G34 (VAG-M2TM) was synthesized using Fmoc chemistry at elevated temperature (75°C for both coupling and deprotection) in a semiautomated Quest synthesizer using Rink Amide Chemmatrix resin (Matrix Innovation Inc, Canada). Coupling reagent were 5 eq amino acid, 5 eq HCTU, 10 eq DIEA in NMP for 5 mins coupling. 5% piperazine and 0.1 M HOBt in DMF were used as the deprotection solution in order to minimize aspartamide formation. The peptide was cleaved from the resin using 95% TFA, 2.5% Tris, 2.5% H₂O and precipitated from ether after removal of TFA. Ether was decanted after centrifugation and the peptide was washed with cold ether again. The final peptide was dissolved in 50% B′ (59.9% isopropanol, 30% acetonitrile, 10% H₂O, and 0.1% TFA) and 50% A (99.9% H₂O, 0.1% TFA) and purified by preparative C4 reverse phase HPLC with a linear gradient of 70% B′ to 85% B′. The peptide was eluted at 78% B′. The purity and identify of the peptide was confirmed by analytical HPLC (>98% purity) and MALDI-MS. Calculated MS: 2782.38, Observed MS: 2782.90.

Cady S.D., Wang J., Wu Y., DeGrado W.F, & Hong M. (2011). Specific Binding of Adamantane Drugs and Direction of their Polar Amines in the Pore of the Influenza M2 Transmembrane Domain in Lipid Bilayers and Dodecylphosphocholine Micelles Determined by NMR Spectroscopy. Journal of the American Chemical Society, 133(12), 4274-4284.

Publication 2011

1-hydroxybenzotriazole acetonitrile Amino Acids Centrifugation Cold Temperature Ethers Fever High-Performance Liquid Chromatographies Isopropyl Alcohol N,N-diisopropylethylamine Peptides Piperazine Resins, Plant Rink amide resin Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Tromethamine

Synthesis of (-)-9 Rocaglate Derivative

A round bottom flask was charged with (-)-rocaglaic acid (27.0 mg, 0.06 mmol), CH₂Cl₂(4 mL), EDCI (16 mg, 0.08 mmol), HOBt (11 mg, 0.07 mmol), methoxylamine hydrochloride (24 mg, 0.28 mmol), and triethylamine (39 uL, 0.28 mmol), and was stirred at room temperature for 12 h. The reaction was quenched with 1M HCl, concentrated, and purified by flash chromatography (gradient elution 50% to 100% ethyl acetate in hexanes) to afford a (-)-9 as white solid (14 mg, 49%). ¹H NMR (500 MHz, CD₃ OD) δ 7.15 (d, J = 9.0 Hz, 2H), 7.09 – 6.99 (m, 3H), 6.94 (d, J = 6.9 Hz, 2H), 6.64 (d, J= 9.0 Hz, 2H), 6.32 (d, J = 1.9 Hz, 1H), 6.21 (d, J= 1.9 Hz, 1H), 4.79 (d, J = 6.2 Hz, 1H), 4.32 (d, J= 14.2 Hz, 1H), 3.87 (s, 1H), 3.85 (s, 1H), 3.72 (dd, J= 14.2, 6.2 Hz, 1H), 3.69 (s, 1H), 3.60 (s, 1H); HRMS calcd for [C₂₈H₂₉NO₈Na]⁺ requires m/z 530.1791; found 530.1772 (ES+).; [a]_D²⁰ = -38.4 (c0.5, CH₃OH, at >98% ee).

Rodrigo C.M., Cencic R., Roche S.P., Pelletier J, & Porco JA J.r. (2011). Synthesis of Rocaglamide Hydroxamates and Related Compounds as Eukaryotic Translation Inhibitors: Synthetic and Biological Studies. Journal of Medicinal Chemistry, 55(1), 558-562.

Publication 2011

1-hydroxybenzotriazole 1H NMR Acids Chromatography ethyl acetate Hexanes methoxyamine hydrochloride triethylamine

Synthesis and Purification of Functionalized Peptides

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Publication 2009

1-hydroxybenzotriazole acetonitrile Amides Biotin Ethyl Ether glycyl-glycyl-glycine High-Performance Liquid Chromatographies Ligands Peptide Biosynthesis Peptides Powder Resins, Plant Wang resin

Synthesis of PEG-Dendritic Polylysine-Cholic Acid Telodendrimer

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Publication 2009

1-hydroxybenzotriazole Cholic Acid Common Cold Dendrites Esters Ethers Lysine piperidine Polylysine Powder Vacuum

Synthesis and Characterization of PEGylated Conjugates

N-α-Fmoc protected amino acids, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) and 2-Cl-trityl chloride resin (100–200 mesh, 1.27 mmol/g) were from EMD Biosciences (San Diego, CA). Papain (EC 3.4.22.2, from papaya latex) and cathepsin B (EC 3.4.22.1, from bovine spleen) were from Sigma-Aldrich (St. Louis, MO). Bis-MAL-dPEG3 (bis-[1,13-(3-maleimidopropionyl)amido]-4,7,10-trioxatridecane, CAS# 756525-89-0) was purchased from Quanta Biodesign (Powell, OH). 1-Hydroxybenzotriazole (HOBt) was purchased from AnaSpec (Fremont, CA). N,N′-Diisopropylcarbodiimide (DIC), 2,2,2-trifluoroethanol (TFE) and all other reagents and solvents were from Sigma-Aldrich (St. Louis, MO). Doxorubicin (DOX) was a kind gift from Meiji Seika Kaisha Ltd. Tokyo, Japan. HPMA,14 4-cyanopentanoic acid dithiobenzoate15 were synthesized according to literature. N-Methacryloylglycylphenylalanylleucylglycyl-doxorubicin (MA-GFLG-DOX) was prepared by the reaction N-methacryloylglycylphenylalanylleucylglycine 4-nitrophenyl ester (MA-GFLG-ONp) with doxorubicin hydrochloride in DMF in the presence of diisopropylethylamine according to the described procedure.16
UV-vis spectra were measured on a Varian Cary 400 Bio UV-visible spectrophotometer. Mass spectra were measured on an FTMS mass spectrometer (LTQ-FT, ThermoElectron, Waltham, MA). ¹H-NMR spectra were recorded on a Mercury400 spectrometer using DMSO-d₆ as the solvent. Polymerization conversion was determined by the measurement of remaining HPMA monomer concentration at different time points using RP-HPLC (Agilent Technologies 1100 series, Zorbax C8 column 4.6×150 mm) with gradient elution from 2 to 90% of Buffer B within 30 min at flow rate of 1.0 mL/min (Buffer A: deionized water (DI H₂O) with 0.1% TFA, Buffer B: acetonitrile with 0.1% TFA). The molecular weight and polydispersity index (PDI) of polymers were measured on an ÄKTA FPLC (fast protein liquid chromatography) system (GE Healthcare, formerly Amersham) equipped with miniDAWN TREOS and OptilabEX detectors (Wyatt Technology, Santa Barbara, CA) using a Superose 6 or 12 HR10/30 column with PBS (pH 7.3) as the mobile phase. Narrow polydispersity polyHPMA fractions prepared by size exclusion chromatography, whose molecular weights were characterized by multiangle light scattering, were used as molecular weight standards. The multiblock polymers were fractionated on the same FPLC system using Superose 6 HR16/60 preparative column. PBS was used as the mobile phase. The flow rate was 1 mL/min. the fraction was collected every 10 min. The salt in the fractions was removed by dialysis. The narrow polydispersity polymer fractions were obtained after freeze-drying.

Pan H., Yang J., Kopečková P, & Kopeček J. (2010). Backbone Degradable Multiblock N-(2-Hydroxypropyl)methacrylamide Copolymer Conjugates via Reversible Addition Fragmentation Chain Transfer Polymerization and Thiol-ene Coupling Reaction. Biomacromolecules, 12(1), 247-252.

Publication 2010

1-hydroxybenzotriazole 1H NMR acetonitrile Acids Amino Acids Bos taurus Buffers Carica papaya Cathepsin B Dialysis Doxorubicin Duxon Esters Gel Chromatography High-Performance Liquid Chromatographies Hydrochloride, Doxorubicin hydroxypropyl methacrylate Latex Light Liquid Chromatography Mass Spectrometry Papain Polymerization Polymers Proteins Resins, Plant Sodium Chloride Solvents Spleen Sulfoxide, Dimethyl Trifluoroethanol trityl chloride

Most recents protocols related to «1-hydroxybenzotriazole»

Synthesis of Triazolopyrimidine Derivatives

Not available on PMC !

Example 2

[Figure (not displayed)]

N-(2-chloro-4-(trifluoromethyl)phenyl)-2-(5-ethyl-2-morpholino-7-oxo-6-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide (Intermediate B) (200 mg, 352 μmol) was suspended in DMF (5 mL). Perfluorophenyl 3-hydroxypicolinate (Intermediate CT) (215 mg, 703 μmol) and Et₃N (97.0 μL, 703 μmol) were added and the RM was stirred at 70° C. for 3 hours. The RM was concentrated under reduced pressure. The crude product was first purified by column chromatography (Silica gel column: Silica 12 g, eluent DCM:MeOH 100:0 to 90:10). Then a second purification by reverse phase preparative HPLC (RP-HPLC acidic 9: 40 to 50% B in 2 min, 50 to 55% B in 10 min) afforded the title compound.

LC-MS: Rt=0.98 min; MS m/z [M+H]⁺ 690.6/692.6, m/z [M−H]⁻ 688.4/690.3; UPLC-MS 1

LC-MS: Rt=4.84 min; MS m/z [M+H]⁺ 690.2/692.2 m/z [M−H]⁻ 688.3/690.3; UPLC-MS 2

¹H NMR (400 MHz, DMSO-d₆) δ 10.37 (s, br, 1H), 10.34 (s, br, 1H), 8.05 (m, 2H), 7.96 (d, J=2.1 Hz, 1H), 7.72 (dd, J=2.1 Hz, 8.7 Hz, 1H), 7.28 (m, 2H), 5.21 (s, 2H), 4.53 (m, 1H), 3.66 (m, 4H), 3.46 (m, 3H), 3.38 (m, 4H), 3.20 (m, 1H), 2.92 (m, 3H), 2.76 (m, 1H), 2.58 (m, 1H), 1.16 (t, J=7.5 Hz, 3H)

Example 24

[Figure (not displayed)]

To the stirred solution of N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)-2-(5-ethyl-2-(4-methoxycyclohex-1-en-1-yl)-7-oxo-6-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide (Intermediate Y) (300 mg, 504 μmol), 4-chloro-3-hydroxypicolinic acid (140 mg, 807 μmol), HOBt (136 mg, 1.01 mmol) and EDC.HCl (193 mg, 1.01 mmol) in DCM (20 mL) was added pyridine (122 μL, 1.51 mmol) at 0° C. The RM was stirred at RT for 16 hours. The RM was quenched with NaHCO₃and extracted with DCM. The organic layer was dried over Na₂SO₄and concentrated under reduced pressure. The crude product was purified by column chromatography (Silica gel column: Silica 4 g, eluent DCM:MeOH 100:0 to 98:2). The residue was purified by preparative chiral HPLC (instrument: Agilent 1200 series, with single quad mass spectrometer; column: LUX CELLULOSE-4, 250 mm×21.1 mm, 5.0 μm; eluent: A=hexane, B=0.1% HCOOH in EtOH; flow rate: 15 mL/min; detection: 210 nm; injection volume: 0.9 mL; gradient: isocratic: 50(A):50(B)).

Example 24a: The product containing fractions were concentrated at 40° C. and washed with n-pentane (5×10 mL), decanted and dried to give the title compound as an off-white solid—first eluting stereoisomer.

Chiral HPLC (C-HPLC 2): Rt=10.764 min

LC-MS: Rt=1.08 min; MS m/z [M+H]⁺ 750.5/752.5, m/z [M−H]⁻ 748.4/750.4; UPLC-MS 1

LC-MS: Rt=5.29 min; MS m/z [M+H]⁺ 750.2/752.2, m/z [M−H]⁻ 748.2/750.2; UPLC-MS 2

¹H NMR (400 MHz, DMSO-d₆) δ 10.68 (s, br, 2H), 8.56 (d, J=8.1 Hz, 1H), 7.98 (d, J=5.6 Hz, 1H), 7.94 (d, J=8.1 Hz, 1H), 7.50 (d, J=5.1 Hz, 1H), 6.72 (m, 1H), 5.34 (s, 2H), 4.53 (m, 1H), 3.52 (m, 4H), 3.28 (m, 4H), 2.98 (m, 3H), 2.80 (m, 1H), 2.63 (m, 1H), 2.55 (m, 1H), 2.46 (m, 1H), 2.16 (m, 2H), 1.95 (m, 1H), 1.68 (m, 1H), 1.17 (t, J=7.3 Hz, 3H)

Example 24b: The product containing fractions were concentrated at 40° C. and washed with n-pentane (5×10 mL), decanted and dried to give the title compound as an off-white solid—second eluting stereoisomer.

Chiral HPLC (C-HPLC 2): Rt=18.800 min

LC-MS: Rt=1.08 min; MS m/z [M+H]⁺ 750.1/752.1, m/z [M−H]⁻ 748.2/750.2; UPLC-MS 1

LC-MS: Rt=5.30 min; MS m/z [M+H]⁺ 750.1/752.1, m/z [M−H]⁻ 748.2/750.2; UPLC-MS 2

¹H NMR (400 MHz, DMSO-d₆) δ 10.83 (s, br, 1H), 10.55 (s, br, 1H), 8.56 (d, J=8.2 Hz, 1H), 8.06 (d, J=5.3 Hz, 1H), 7.92 (d, J=8.2 Hz, 1H), 7.55 (d, J=5.3 Hz, 1H), 6.72 (m, 1H), 5.35 (s, 2H), 4.54 (m, 1H), 3.54 (m, 4H), 3.28 (m, 3H), 3.25 (m, 1H), 2.99 (m, 3H), 2.81 (m, 1H), 2.62 (m, 1H), 2.41 (m, 2H), 2.16 (m, 2H), 1.96 (m, 1H), 1.66 (m, 1H), 1.18 (t, J=7.3 Hz, 3H)

Example 25

[Figure (not displayed)]

N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)-2-(5-ethyl-2-(4-methoxycyclohex-1-en-1-yl)-7-oxo-6-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide.HCl (Intermediate Y) (120 mg, 190 μmol) and DIPEA (166 μL, 950 μmol) were dissolved in DCM (5 mL) and then 3-hydroxypicolinoyl chloride (Intermediate CV) (59.9 mg, 380 μmol) was added at 0° C. and stirred for 2 hours. 3-hydroxypicolinoyl chloride (Intermediate CV) (59.9 mg, 380 μmol) was added again and the reaction was continued under stirring for 12 hours. The RM was diluted with DCM and washed with water and aq NaHCO₃(2×20 mL), washed with water and brine, dried over Na₂SO₄, filtered and concentrated. The crude product was combined with another experiment and purified by column chromatography (Silica gel column: Silica 4 g, eluent DCM:MeOH 100:0 to 99:1) then further purified by reverse phase preparative HPLC (RP-HPLC acidic 10: 40 to 50% B in 2 min, 50 to 60% B in 8 min) to give the title compound as an off-white solid.

The racemate was purified by preparative chiral HPLC (instrument: Agilent 1200 series, with single quad mass spectrometer; column: CELLULOSE-4, 250 mm×21.2 mm; eluent: A=hexane, B=0.1% HCOOH in MeOH:EtOH 1:1; flow rate: 20 mL/min; detection: 210 nm; injection volume: 0.9 mL; gradient: isocratic 60(A):40(B)).

Example 25a: First eluting stereoisomer, off-white solid.

Chiral HPLC (C-HPLC 1): Rt=10.070 min

LC-MS: Rt=0.98 min; MS m/z [M+H]⁺ 716.5/718.6, m/z [M−H]⁻ 714.3/716.3; UPLC-MS 1

LC-MS: Rt=4.76 min; MS m/z [M+H]⁺ 716.2/718.2, m/z [M−H]⁻ 714.2/716.2; UPLC-MS 2

¹H NMR (400 MHz, DMSO-d₆) δ 10.46 (s, br, 2H), 8.56 (d, J=8.5 Hz, 1H), 8.05 (m, 1H), 7.90 (d, J=8.4 Hz, 1H), 7.28 (m, 2H), 6.72 (m, 1H), 5.30 (s, 2H), 4.54 (m, 1H), 3.47 (m, 4H), 3.27 (s, 3H), 3.21 (m, 1H), 2.96 (m, 3H), 2.79 (m, 1H), 2.59 (m, 3H), 2.43 (m, 1H), 2.14 (m, 1H), 1.95 (m, 1H), 1.67 (m, 1H), 1.17 (t, J=7.2 Hz, 3H)

Example 25b: Second eluting stereoisomer, off-white solid.

Chiral HPLC (C-HPLC 1): Rt=16.023 min

LC-MS: Rt=0.96 min; MS m/z [M+H]⁺ 716.3/718.3, m/z [M−H]⁻ 714.3/716.3; UPLC-MS 1

LC-MS: Rt=4.77 min; MS m/z [M+H]⁺ 716.2/718.2, m/z [M−H]⁻ 714.2/716.2; UPLC-MS 2

¹H NMR (400 MHz, DMSO-d₆) δ 10.39 (s, br, 2H), 8.56 (d, J=8.0 Hz, 1H), 8.06 (m, 1H), 7.93 (d, J=8.1 Hz, 1H), 7.28 (m, 2H), 6.72 (m, 1H), 5.32 (s, 2H), 4.54 (m, 1H), 3.46 (m, 4H), 3.27 (s, 3H), 3.20 (m, 1H), 2.96 (m, 3H), 2.79 (m, 1H), 2.59 (m, 3H), 2.41 (m, 1H), 2.14 (m, 1H), 1.95 (m, 1H), 1.68 (m, 1H), 1.17 (t, J=7.1 Hz, 3H)

US11878973B2. Bicyclic compounds and their uses (2024-01-23). NOVARTIS AG [CH]. Inventors: Vincent Bordas [FR], Jvan Brun [CH], Markus Furegati [CH], Jacques Hamon [FR], Jürgen Hans-Hermann Hinrichs [DE], Philipp Holzer [CH], Fatma Limam [FR], Henrik Möbitz [DE], Sandro Nocito [CH], Simone Plattner [DE], Niko Schmiedeberg [CH], Joseph Schoepfer [CH], Ross Sinclair Strang [FR], Frédéric Zecri [US].

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Patent 2024

1-hydroxybenzotriazole 1H NMR acetamide Acids Bicarbonate, Sodium Bicyclo Compounds brine Cellulose Chlorides Chromatography DIPEA Ethanol H 718 Hexanes High-Performance Liquid Chromatographies Morpholinos pentane Piperazine Pressure pyridine Silica Gel Silicon Dioxide Stereoisomers Sulfoxide, Dimethyl Tandem Mass Spectrometry

Synthesis of Quinoline-Thiazolidine Hybrid Compound

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Example 48

[Figure (not displayed)]

TEA (2.07 mL, 14.8 mmol) was added to a stirred suspension of 6-(3,3-dimethylpyrrolidin-1-yl)quinoline-4-carboxylic acid Intermediate 106 (347 mg, 0.74 mmol), (R)-3-glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (385 mg, 1.86 mmol), HOBt (568 mg, 3.71 mmol) and EDC (711 mg, 3.71 mmol) in MeCN (7 mL) and EtOAc (7 mL) at 7° C. The resulting suspension was stirred at 7° C. overnight. The solvent was removed under reduced pressure. The residue was suspended in EtOAc and washed with a solution of sat NaHCO₃(50 mL). The aqueous layer was extracted with EtOAc (4×50 mL). The organic layers were combined and washed with water (4×20 mL) and concentrated under reduced pressure. The crude product was purified by preparative HPLC, PrepMethod P, to give the title compound (174 mg, 55%) as an orange solid; HRMS (ESI) m/z [M+H]⁺ calcd for C₂₂H₂₆N₅O₂S: 424.1802 found: 424.1806; ¹H NMR (300 MHz, DMSO-d₆) δ 8.91 (t, 1H), 8.53 (d, 1H), 7.84 (d, 1H), 7.34 (d, 1H), 7.29-7.15 (m, 2H), 5.30 (dd, 1H), 4.89 (d, 1H), 4.71 (d, 1H), 4.27 (d, 2H), 3.51-3.33 (m, overlapping with solvent), 3.15 (s, 2H), 1.80 (t, 2H), 1.14 (s, 3H), 1.13 (s, H).

US11858924B2. N-(2-(4-cyanothiazolidin-3-yl)-2-oxoethyl)-quinoline-4-carboxamides (2024-01-02). AstraZeneca AB [SE]. Inventors: Jonas Brånalt [SE], Maria Johansson [SE], Anneli Nordqvist [SE], Marianne Swanson [SE].

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Patent 2024

1-hydroxybenzotriazole 1H NMR Bicarbonate, Sodium High-Performance Liquid Chromatographies Pressure quinoline-4-carboxamide quinoline-4-carboxylic acid Solvents Sulfoxide, Dimethyl

Synthesis of Quinoline-Pyrazole Derivative

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Example 117

[Figure (not displayed)]

DIPEA (3.29 mL, 18.8 mmol) was added to a stirred suspension of crude 6-(6,6-dimethyl-5,6-dihydrocyclopenta[c]pyrazol-2(4H)-yl)quinoline-4-carboxylic acid Intermediate 243 (482 mg, 0.62 mmol), (R)-3-glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (194 mg, 0.94 mmol), HOBt (420 mg, 3.14 mmol) and EDC (596 mg, 3.14 mmol) in MeCN (7 mL) and EtOAc (7 mL) at 15° C. The resulting solution was stirred at 50° C. for 2 h. The solvent was removed under reduced pressure and the residue was partitioned between sat NaHCO₃(aq, 60 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (5×100 mL). The organic layers were combined and washed with H₂O (3×50 mL). The organic layer was dried over Na₂SO₄, filtered and evaporated. The residue was purified by preparative HPLC, PrepMethod F, (gradient 42-52%) to give the title compound (0.14 g, 49%) as a white solid; HRMS (ESI) m/z [M+H]⁺ calcd for C₂₄H₂₅N₆O₂S: 461.1754, found: 461.1742; ¹H NMR (300 MHz, DMSO-d₆) δ 9.14 (t, 1H), 8.92 (d, 1H), 8.70 (d, 1H), 8.31 (dd, 1H), 8.22 (s, 1H), 8.13 (d, 1H), 7.58 (d, 1H), 5.44-5.24 (m, 1H), 4.90 (d, 1H), 4.72 (d, 1H), 4.36 (d, 2H), 3.46-3.30 (m, overlapping with solvent), 2.66 (t, 2H), 2.19 (t, 2H), 1.30 (s, 6H).

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Patent 2024

1-hydroxybenzotriazole 1H NMR Bicarbonate, Sodium DIPEA High-Performance Liquid Chromatographies Pressure pyrazole quinoline-4-carboxamide quinoline-4-carboxylic acid Solvents Sulfoxide, Dimethyl

Synthesis of N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)-2-(5-ethyl-7-oxo-6-(piperazin-1-yl)-2-(pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide

Not available on PMC !

Example 18

[Figure (not displayed)]

To the stirred solution of 3-hydroxypicolinic acid (166 mg, 1.19 mmol), EDC.HCl (228 mg, 1.19 mmol), HOBt (161 mg, 1.19 mmol) in DMF (3 mL) was added N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)-2-(5-ethyl-7-oxo-6-(piperazin-1-yl)-2-(pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide (Intermediate Q) (330 mg, 596 μmol) and DIPEA (624 μL, 3.57 mmol) and the RM was at RT for 16 hours. The RM was concentrated under reduced pressure and water was added. The resultant brown solid was filtered off and dried under vacuum. The crude product was purified by reverse phase preparative HPLC (RP-HPLC acidic 4: 35 to 40% B in 2 min, 40 to 45% B in 10 min) to give the title compound.

LC-MS: Rt=0.94 min; MS m/z [M+H]⁺ 675.3/677.3, m/z [M−H]⁻ 673.3/675.3; UPLC-MS 1

LC-MS: Rt=4.68 min; MS m/z [M+H]⁺ 675.2/677.2, m/z [M−H]⁻ 673.2/675.2; UPLC-MS 2

¹H NMR (400 MHz, DMSO-d₆) δ 10.54 (s, br, 1H), 10.38 (s, br, 1H), 8.55 (d, J=8.4 Hz, 1H), 8.06 (m, 1H), 7.95 (d, J=8.4 Hz, 1H), 7.28 (m, 2H), 5.25 (s, 2H), 4.53 (m, 1H), 3.46 (m, 3H), 3.35 (m, 4H), 3.19 (m, 1H), 2.91 (m, 3H), 2.75 (m, 1H), 2.57 (m, 1H), 1.89 (m, 4H), 1.15 (t, 3H)

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Patent 2024

1-hydroxybenzotriazole 1H NMR acetamide Acids DIPEA High-Performance Liquid Chromatographies Piperazine Pressure Sulfoxide, Dimethyl Tandem Mass Spectrometry Vacuum

Synthesis of Quinoline-Based Derivatives

Not available on PMC !

Example 110

[Figure (not displayed)]

To a vial were added (S)-2-((1-(7,8-dichloro-4-(1H-imidazol-1-yl)quinolin-2-yl)pyrrolidin-2-yl)methoxy)acetic acid (30 mg, 0.0712 mmol, 1.0 eq.), NH₄Cl (19 mg, 0.356 mmol, 5.0 eq.), EDC·HCl (27 mg, 0.142 mmol, 2.0 eq.), HOBt (9.6 mg, 0.0712 mmol, 1.0 eq), DMF (0.5 mL). With stirring, DIPEA (0.062 mL, 0.356 mmol, 5.0 eq.) was added and the reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate (20 mL), washed with H₂O (3×10 mL), brine (10 mL), dried over Na₂SO₄. After concentration, the residue was purified by silica gel chromatography to afford the title product. MS: [M+1]⁺420.

The following compounds are prepared essentially by the same methods as described above for I-760.

ExampleStarting MaterialStructure[M + 1]⁺

I-761[Figure (not displayed)]
NH₂OH·HC1[Figure (not displayed)]
436

I-762[Figure (not displayed)]
NH₂CN[Figure (not displayed)]
445

US11873291B2. Quinoline cGAS antagonist compounds (2024-01-16). ImmuneSensor Therapeutics, Inc. [US], The Board of Regents of the University of Texas System [US]. Inventors: Jian Qiu [US], Qi Wei [US], Matt Tschantz [US], Heping Shi [US], Youtong Wu [US], Hulling Tan [US], Lijun Sun [US], Chuo Chen [US], Zhijian Chen [US].

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Patent 2024

1-hydroxybenzotriazole acetamide Acetic Acid Anabolism brine Chromatography DIPEA ethyl acetate Gel Chromatography imidazole Silica Gel Silicon Dioxide

Top products related to «1-hydroxybenzotriazole»

1 hydroxybenzotriazole hydrate by Merck Group

Sourced in United States, Germany

1-hydroxybenzotriazole hydrate is a laboratory reagent primarily used as a coupling agent in peptide synthesis. It functions as an activator for the formation of peptide bonds between amino acids. The product is available in various purities and packaging sizes to meet the needs of researchers and scientists working in the fields of organic chemistry, biochemistry, and peptide synthesis.

Trifluoroacetic acid by Merck Group

Sourced in United States, Germany, United Kingdom, France, Spain, Italy, Australia, China, India, Sao Tome and Principe, Poland, Canada, Switzerland, Macao, Belgium, Netherlands, Czechia, Japan, Austria, Brazil, Denmark, Ireland

Trifluoroacetic acid is a colorless, corrosive liquid commonly used as a reagent in organic synthesis and analytical chemistry. It has the chemical formula CF3COOH.

Piperidine by Merck Group

Sourced in United States, Germany, Australia, Italy, France, Hungary, Canada, Poland, Sao Tome and Principe

Piperidine is a colorless, flammable liquid organic compound with the chemical formula C₅H₁₁N. It is a heterocyclic amine that is widely used as a building block in the synthesis of various pharmaceutical and industrial chemicals.

1 hydroxybenzotriazole by Merck Group

Sourced in United States, Hungary

1-Hydroxybenzotriazole is a chemical compound used as a coupling agent in organic synthesis. It serves to activate carboxylic acids, facilitating their reaction with amines to form amide bonds. This compound is commonly employed in peptide synthesis and other organic reactions.

Fetal bovine serum (fbs) by Thermo Fisher Scientific

Sourced in United States, China, United Kingdom, Germany, Australia, Japan, Canada, Italy, France, Switzerland, New Zealand, Brazil, Belgium, India, Spain, Israel, Austria, Poland, Ireland, Sweden, Macao, Netherlands, Denmark, Cameroon, Singapore, Portugal, Argentina, Holy See (Vatican City State), Morocco, Uruguay, Mexico, Thailand, Sao Tome and Principe, Hungary, Panama, Hong Kong, Norway, United Arab Emirates, Czechia, Russian Federation, Chile, Moldova, Republic of, Gabon, Palestine, State of, Saudi Arabia, Senegal

Fetal Bovine Serum (FBS) is a cell culture supplement derived from the blood of bovine fetuses. FBS provides a source of proteins, growth factors, and other components that support the growth and maintenance of various cell types in in vitro cell culture applications.

Trifluoroacetic acid tfa by Merck Group

Sourced in United States, Germany, United Kingdom, France, China, Italy, Switzerland, Sao Tome and Principe, Spain, Australia, Poland, Macao, Belgium, Sweden, Hungary, Netherlands, Ireland

Trifluoroacetic acid (TFA) is a colorless, corrosive liquid used in various laboratory applications. It is a strong organic acid with a chemical formula of CF3COOH. TFA is commonly utilized as a reagent or solvent in various chemical processes, including protein and peptide synthesis, sample preparation, and chromatographic techniques.

Dimethyl sulfoxide (dmso) by Merck Group

Sourced in United States, Germany, United Kingdom, China, Italy, Sao Tome and Principe, France, Macao, India, Canada, Switzerland, Japan, Australia, Spain, Poland, Belgium, Brazil, Czechia, Portugal, Austria, Denmark, Israel, Sweden, Ireland, Hungary, Mexico, Netherlands, Singapore, Indonesia, Slovakia, Cameroon, Norway, Thailand, Chile, Finland, Malaysia, Latvia, New Zealand, Hong Kong, Pakistan, Uruguay, Bangladesh

DMSO is a versatile organic solvent commonly used in laboratory settings. It has a high boiling point, low viscosity, and the ability to dissolve a wide range of polar and non-polar compounds. DMSO's core function is as a solvent, allowing for the effective dissolution and handling of various chemical substances during research and experimentation.

Sodium hydroxide (naoh) by Merck Group

Sourced in Germany, United States, India, United Kingdom, Italy, China, Spain, France, Australia, Canada, Poland, Switzerland, Singapore, Belgium, Sao Tome and Principe, Ireland, Sweden, Brazil, Israel, Mexico, Macao, Chile, Japan, Hungary, Malaysia, Denmark, Portugal, Indonesia, Netherlands, Czechia, Finland, Austria, Romania, Pakistan, Cameroon, Egypt, Greece, Bulgaria, Norway, Colombia, New Zealand, Lithuania

Sodium hydroxide is a chemical compound with the formula NaOH. It is a white, odorless, crystalline solid that is highly soluble in water and is a strong base. It is commonly used in various laboratory applications as a reagent.

N n dimethylformamide (dmf) by Merck Group

Sourced in United States, Germany, United Kingdom, China, Italy, Canada, India, Australia, Japan, Spain, Singapore, Sao Tome and Principe, Poland, France, Switzerland, Macao, Chile, Belgium, Czechia, Hungary, Netherlands

N,N-dimethylformamide is a clear, colorless liquid organic compound with the chemical formula (CH3)2NC(O)H. It is a common laboratory solvent used in various chemical reactions and processes.

Pyridine by Merck Group

Sourced in United States, Germany, China, United Kingdom, France, Italy, Poland, Spain, Australia, India, Sao Tome and Principe, Switzerland, Canada, Singapore, Japan, Macao, Panama

Pyridine is a colorless, flammable liquid used as a solvent and as an intermediate in the production of various organic compounds. It has a distinctive pungent odor. Pyridine is commonly employed in chemical synthesis, pharmaceuticals, and the production of other industrial chemicals.

What are some common applications of 1-hydroxybenzotriazole?

1-Hydroxybenzotriazole is a versatile reagent used in a variety of organic synthesis applications, particularly in peptide chemistry and enzyme catalysis. It is commonly used as an activator for carboxylic acids, enabling efficient coupling reactions. This heterocyclic compound can enhance the reactivity and selectivity of various chemical transformations, making it a valuable tool for chemical researchers.

How can 1-hydroxybenzotriazole be used to optimize chemical reactions?

1-Hydroxybenzotriazole can improve the efficiency and selectivity of chemical reactions in several ways. It serves as an activator for carboxylic acids, facilitating coupling reactions and enabling the formation of amide bonds. Additionally, 1-hydroxybenzotriazole can enhance the reactivity of other functional groups, leading to more precise and controllable transformations. Researchers can leverage this versatile reagent to streamline their organic synthesis workflows and achieve better results.

What are some common challenges in using 1-hydroxybenzotriazole, and how can PubCompare.ai help?

One of the key challenges in using 1-hydroxybenzotriazole is identifying the most effective protocols from the vast array of literature, pre-prints, and patents. PubCompare.ai can assist researchers by efficiently screening protocol literature and leveraging AI to pinpoint critical insights. The platform's AI-driven analysis can highlight key differences in protocol effectiveness, enabling researchers to choose the best option for reproducibility and accuracy in their 1-hydroxybenzotriazole-related studies. This can help researchers save time, reduce the risk of experimental failures, and optimize their use of this valuable reagent.

Are there different variations or types of 1-hydroxybenzotriazole, and how do they differ?

Yes, there are several variations of 1-hydroxybenzotriazole that researchers may encounter. For example, 1-hydroxy-7-azabenzotriazole (HOAt) is a structurally similar compound that can offer different reactivity profiles and selectivity in certain applications. Additionally, there are resin-bound versions of 1-hydroxybenzotriazole that are designed for solid-phase synthesis. Researchers should carefuully evaluate the specific properties and suitability of different 1-hydroxybenzotriazole derivatives for their particular research needs.

How can PubCompare.ai help streamline 1-hydroxybenzotriazole-related research?

PubCompare.ai can significantly streamline 1-hydroxybenzotriazole-related research in several ways. The platform allows researchers to efficiently screen protocol literature, leveraging AI to pinpoint critical insights that can help identify the most effective protocols for their specific research goals. PubCompare.ai's AI-driven analysis can highlight key differences in protocol effectiveness, enabling researchers to choose the best option for reproducibility and accuracy. This can save researchers time, reduce the risk of experimental failures, and optimize their use of this valuable reagent. By empowering researchers with AI-assisted decision-making, PubCompare.ai can enhance the efficiency and success of 1-hydroxybenzotriazole-related studies.

More about "1-hydroxybenzotriazole"

1-Hydroxybenzotriazole (HOBt) is a versatile heterocyclic compound widely used in organic synthesis, particularly in peptide chemistry and enzyme catalysis.
This versatile reagent serves as an activator for carboxylic acids, enabling efficient coupling reactions.
HOBt enhances the reactivity and selectivity of various transformations, making it a valuable tool for chemical researchers.
HOBt hydrate, a related compound, is also commonly utilized in similar applications.
Researchers often employ additional reagents like trifluoroacetic acid (TFA), piperidine, and solvents such as DMSO, N,N-dimethylformamide, and pyridine in conjunction with HOBt to facilitate various chemical reactions and transformations.
PubCompare.ai, an AI-driven platform, can optimize your 1-hydroxybenzotriazole research by helping you locate the best protocols from literature, preprints, and patents.
The seamless comparison features allow you to identify the most reproducible and effective methods, streamlining your HOBt-related studies.
Experience the power of AI-assisted research with PubCompare.ai and take your 1-hydroxybenzotriazole projects to new heights.