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DIPEA

DIPEA (N,N-Diisopropylethylamine) is a versatile organic compound used extensively in chemical synthesis and research.
This tertiary amine serves as a non-nucleophilic base, aiding in various reactions and assisting with the deprotonation of acidic substrates.
DIPEA is particularly valuable in the fields of organic chemistry, medicinal chemistry, and materials science, where it helps facilitate the formation of carbon-carbon bonds, protect functional groups, and catalyze important transformations.
Researchers can leverage the power of AI-driven DIPEA research optimization with PubCompare.ai to effortlessly locate the best protocols from literature, preprints, and patents, unleashing their research potential and finding the optimal DIPEA solutions for their projects.
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Most cited protocols related to «DIPEA»

Synthesis of Arginine-Grafted Bioreducible Poly(Disulfide Amine)

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Publication 2008

1H NMR Acrylamide Amines Anabolism Arginine Atmosphere Bath Biological Assay Dialysis DIPEA Disulfides Ethyl Ether Freeze Drying Moles Nitrogen piperidine Poly A Polymerization Polymers Tissue, Membrane Vertebral Column

UHPLC-MS/MS Analysis of Redox Cycling Metabolites

An UltiMate 3000 quaternary UHPLC equipped with a refrigerated autosampler (6 °C) and a column heater was used. Both gradients used a Phenomenex Synergy Polar-RP column (150 × 2 mm i.d., 4 µm; 80 Å, Phenomenex, Torrance, CA) at a flow rate of 0.2 mL/min. Solvent A was 5 mM DIPEA and 200 mM HFIP and solvent B was methanol with 5 mM DIPEA 200 mM HFIP. The linear gradient 1 was as follows: 100 % A for 6 min, 98 % A at 8 min, 86 % A at 12 min, 50 % A at 14 min and 10 % A at 15 min. 10 % A was held for 4 min, back to 100 % A over 1 min prior to a 5 min equilibration. Linear gradient 2 was shorter, in order to run the unstable redox cycling metabolites (NAD⁺, NADH, NADP⁺ and NADPH) as quickly as possible after the extractions. 100 % A for 2 min, 80 % A at 4 min, 10 % A at 6 min, and 10 % A at 8 min. 10 % A was held for 2 min, back to 100 % A over 1 min prior to a 4 min equilibration. The separations were performed at 55 °C. MS analysis was conducted on a Thermo Scientific TSQ Quantum Ultra AM mass spectrometer (Thermo Scientific, San Jose, CA, USA) equipped with a HESI II source operating in negative mode. The TSQ Quantum operating conditions were as follows: spray voltage 4000 V; vaporizer temperature 200 °C; capillary temperature 350 °C; tube lens 90 V. The sheath gas (nitrogen) and auxiliary gas (nitrogen) pressures were 45 and 10 (arbitrary units), respectively. Both Q1 and Q3 resolutions were set at 0.7 amu. Scan width was 0.002 and the dwell time was 20 msec. Collision-induced dissociation used argon as the collision gas at 1.5 mTorr. The collision energy was optimized for each metabolite and the values are reported in Table 1. Data analysis was done with Xcalibur software 2.6. Statistical analysis was performed in Microsoft Excel or Prism v6 (GraphPad Software Inc. La Jolla, CA).

Guo L., Worth A.J., Mesaros C., Snyder N.W., Glickson J.D, & Blair I.A. (2016). Diisopropylethylamine/hexafluoroisopropanol-mediated ion-pairing UHPLC-MS for phosphate and carboxylate metabolite analysis: utility for studying cellular metabolism. Rapid communications in mass spectrometry : RCM, 30(16), 1835-1845.

Publication 2016

A-A-1 antibiotic Argon ARID1A protein, human Capillaries DIPEA Lens, Crystalline Methanol NADH NADP Nitrogen Oxidation-Reduction prisma Radionuclide Imaging Solvents Vaporizers

Radiosynthesis of 18F-Labeled RGD Peptides

¹⁸F-NFP was synthesized as previously reported with HPLC purification [30 (link), 33 (link)]. As a typical procedure for all the ¹⁸F-FP-RGD peptides, ¹⁸F-FP-SRGD2 was synthesized as follows: the HPLC-purified ¹⁸F-NFP was rotary-evaporated to dryness, redis solved in DMSO (200 μL), and added to a solution of SRGD2 (1.0 μmol) and DIPEA (20 μL). The reaction mixture was allowed to incubate at 60°C for 30 min. After dilution with 2 mL of water and 0.1% TFA, the mixture was injected into the semipreparative HPLC. The collected fractions containing ¹⁸F-FP-SRGD2 were combined and rotary-evaporated to remove MeCN and TFA (the radiochemical yields and radio-HPLC retention time were shown in the “Electronic Supplementary Materials”). The activity was then reconstituted in normal saline and passed through a 0.22-μm Millipore filter into a sterile multidose vial for in vivo experiments.
¹⁸F-SFB was synthesized by an automated protocol developed in our research lab using a commercially available synthesis module (GE TRACERlab FX_FN; GE Healthcare; detailed procedure to be published elsewhere). The purified ¹⁸F-SFB were rotary-evaporated to dryness, redissolved in DMSO (200 μL), and added to a solution of SRGD2 (1.0 μmol) and DIPEA (20 μL). The reaction mixture was allowed to incubate at 60°C for 30 min. After dilution with 2 mL of 0.1% TFA water, the mixture was injected into the semipreparative HPLC. The collected fractions containing ¹⁸F-FB-SRGD2 were combined and rotary-evaporated to remove MeCN and TFA (the radiochemical yields and radio-HPLC retention time were shown in the “Electronic Supplementary Materials”). The activity was then reconstituted in normal saline and passed through a 0.22-μm Millipore filter into a sterile multidose vial for in vivo experiments.

Liu S., Liu Z., Chen K., Yan Y., Watzlowik P., Wester H.J., Chin F.T, & Chen X. (2009). 18F-Labeled Galacto and PEGylated RGD Dimers for PET Imaging of αvβ3 Integrin Expression. Molecular imaging and biology : MIB : the official publication of the Academy of Molecular Imaging, 12(5), 530-538.

Publication 2009

Anabolism arginyl-glycyl-aspartic acid DIPEA High-Performance Liquid Chromatographies N-succinimidyl-4-fluorobenzoate Normal Saline Radiopharmaceuticals Retention (Psychology) Sterility, Reproductive Sulfoxide, Dimethyl Technique, Dilution

LC-HRMS Analysis of Biomolecules

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Publication 2018

Capillaries DIPEA isolation Lens, Crystalline Liquid Chromatography Methanol Nitrogen Radionuclide Imaging Solvents Spectrometry Vaporizers

Heterocyclic Carboxamide Synthesis

β-naltrexamine (100 mg, 0.29 mmol), heterocyclic carboxylic acid (0.58 mmol) and BOP (258 mg, 0.58 mmol) were dissolved in DCM (5 mL). To this solution, DIPEA (150 mL, 0.81 mmol) was added and the mixture was stirred at room temperature for 3 to 16 hours. The solution was concentrated under reduced pressure and the residue was taken up in MeOH (5 mL), and K₂CO₃ was added (300 mg). After 1 hour at room temperature, the mixture was concentrated to dryness. The final crude was purified by SiO₂ chromatography to afford the target compound.
The title compound was then subsequently converted into the HCl salt for biological testing.

Le Naour M., Lunzer M.M., Powers M.D, & Portoghese P.S. (2012). Opioid activity of spinally selective analogues of N-Naphthoyl-β-naltrexamine (NNTA) in HEK-293 cells and mice. Journal of medicinal chemistry, 55(2), 670-677.

Publication 2012

beta-naltrexamine Biopharmaceuticals Chromatography DIPEA Heterocyclic Acids potassium carbonate Pressure Sodium Chloride

Most recents protocols related to «DIPEA»

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 (S)-3-Hydroxy-N-methylbutanamido Indazole Derivative

Not available on PMC !

Example 110

[Figure (not displayed)]

HATU (89 mg, 0.23 mmol) was added to DIPEA (103 μL, 0.59 mmol), (S)-3-hydroxybutanoic acid (20.4 mg, 0.20 mmol) and 6-methoxy-2-((1r,4r)-4-(methylamino)cyclohexyl)-N-(pyrazolo[1,5-c]pyrimidin-3-yl)-2H-indazole-5-carboxamide hydrochloride (Int V-4) (70 mg, 0.13 mmol) in DMF (6 mL). The resulting mixture was stirred at 25° C. for 15 h. The crude product was purified directly by C18-flash chromatography (eluting with 0-100% MeCN in water (0.1% NH₄·OH) and further purified by prep. HPLC (YMC-Actus Triart C18 ExRS 5 μm, 30×150 mm; elution gradient: 9-42% MeCN in water (10 mM NH₄HCO₃+0.1% NH₄OH); 60 mL/min) to afford 2-((1S,4r)-4-((S)-3-hydroxy-N-methylbutanamido)cyclohexyl)-6-methoxy-N-(pyrazolo[1,5-c]pyrimidin-3-yl)-2H-indazole-5-carboxamide (37 mg, 55.7%), as a yellow solid. ¹H NMR (300 MHz, DMSO-d₆) (mixture of rotamers) δ 10.34 (s, 1H), 9.09-9.01 (m, 1H), 8.72 (s, 1H), 8.58-8.49 (m, 2H), 8.46 (d, 1H), 7.19 (d, 1H), 7.04 (s, 1H), 4.62 (d, 1H), 4.56-4.37 (m, 1.5H), 4.04 (s, 4H), 3.92-3.81 (m, 0.5H) 2.79 (d, 3H), 2.46-2.25 (m, 2H), 2.24-1.95 (m, 4H), 1.92-1.56 (m, 4H), 1.18-1.02 (m, 3H). MS ESI, m/z=506 [M+H]⁺

US11866405B2. Substituted indazoles as IRAK4 inhibitors (2024-01-09). AstraZeneca AB [SE]. Inventors: Ina Terstiege [SE], Stefan Schiesser [SE], Yafeng Xue [SE], Hui-Fang Chang [SE], Anna Ingrid Kristina Berggren [SE].

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Patent 2024

1H NMR 3-Hydroxybutyric Acid Chromatography DIPEA High-Performance Liquid Chromatographies Indazoles inhibitors IRAK4 protein, human Sulfoxide, Dimethyl

Enantioselective Synthesis of Pyrazolo[1,5-a]pyrimidine Indazole Carboxamides

Not available on PMC !

Example 54

[Figure (not displayed)]

To a solution of rac-6-cyclopropoxy-2-(1S,3R)-3-hydroxy-3-methylcyclohexyl)-2H-indazole-5-carboxylic acid (100 mg, 0.3 mmol), HATU (115 mg, 0.3 mmol) and DIPEA (534, 0.3 mmol) in THF (10 mL) under N₂atmosphere was added pyrazolo[1,5-a]pyrimidin-3-amine (Int I-5) (41 mg, 0.3 mmol). The resulting solution was stirred at rt for 2 h. The reaction was quenched with water (1 mL). The mixture was purified directly by prep. chiral-HPLC (Chiralpak® IA, 5 μm 20 mm×250 mm; isocratic with 50% MTBE (0.5% 2N NH₃-MeOH) in MeOH; 50 mL/min) to afford rel-6-cyclopropoxy-2-(1S,3R)-3-hydroxy-3-methylcyclohexyl)-N-(pyrazolo[1,5-a]pyrimidin-3-yl)-2H-indazole-5-carboxamide—Isomer 1 (42 mg, 42%, 100% ee) and rel-6-cyclopropoxy-2-(1S,3R)-3-hydroxy-3-methylcyclohexyl)-N-(pyrazolo[1,5-a]pyrimidin-3-yl)-2H-indazole-5-carboxamide—Isomer 2 (46 mg, 46%, 100% ee), both as yellow solids. The ¹H NMR and MS obtained for both products were identical. ¹H NMR (400 MHz, DMSO-d₆) δ 10.31 (s, 1H), 9.07 (dd, 1H), 8.75 (s, 1H), 8.58 (s, 1H), 8.55 (dd, 1H), 5.53 (s, 1H), 7.51 (s, 1H), 7.05 (dd, 1H), 4.50-4.64 (m, 1H), 4.19-4.25 (m, 1H), 1.94-2.11 (m, 3H), 1.72-1.86 (m, 2H), 1.63 (br. d, 1H), 1.37-1.56 (m, 2H), 1.25 (s, 3H), 1.01-1.11 (m, 2H), 0.93-1.03 (m, 2H). MS ESI, m/z=447 [M+H]⁺.

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Patent 2024

1H NMR Amines Atmosphere Carboxylic Acids DIPEA High-Performance Liquid Chromatographies Indazoles Isomerism methyl tert-butyl ether Sulfoxide, Dimethyl

Synthesis of Quinoline-Pyrazole Derivative

Not available on PMC !

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).

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 DIPEA High-Performance Liquid Chromatographies Pressure pyrazole quinoline-4-carboxamide quinoline-4-carboxylic acid Solvents Sulfoxide, Dimethyl

Synthesis of Quinoline-4-Carboxylic Acid Derivative

Not available on PMC !

Example 182

[Figure (not displayed)]

6-(3-Fluoro-3-phenylazetidin-1-yl)quinoline-4-carboxylic acid Intermediate 343 (22 mg, 0.07 mmol), HATU (39 mg, 0.10 mmol) and DIPEA (48 μL, 0.27 mmol) were mixed in MeCN (1 mL) and EtOAc (1 mL). (R)-3-Glycylthiazolidine-4-carbonitrile hydrochloride Intermediate 4 (17 mg, 0.08 mmol) was added and the reaction mixture was stirred at rt for 1 h. DCM (8 mL) and NaHCO₃(5 mL, aq) were added, and the reaction mixture was stirred, filtered through a phase separator and evaporated under reduced pressure. The crude compound was purified by preparative SFC, PrepMethod SFC-E, (gradient: 30-35%), to give the title compound (2.4 mg, 7%); HRMS (ESI) m/z [M+H]⁺ calcd for C₂₅H₂₃FN₅O₂S: 476.1550, found: 476.1560.

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Patent 2024

Azetidines Bicarbonate, Sodium DIPEA Pressure quinoline-4-carboxamide quinoline-4-carboxylic acid

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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.

N n diisopropylethylamine by Merck Group

Sourced in United States, Germany, Italy, Canada, France, Sao Tome and Principe, Czechia

N,N-diisopropylethylamine is a basic, organic compound commonly used as a reagent in chemical synthesis and laboratory procedures. It functions as a base and serves as a proton acceptor. The compound is colorless and has a characteristic amine-like odor.

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.

Synergi c18 150 by Phenomenex

The Synergi C18 150 is a reversed-phase high-performance liquid chromatography (HPLC) column from Phenomenex. It features a 150 mm length, 4.6 mm internal diameter, and 4 μm particle size. The column is packed with a C18 stationary phase, which is commonly used for the separation and analysis of a wide range of organic compounds.

Cdcl3 by Agilent Technologies

Sourced in United States

CDCl3 is a common deuterated solvent used in nuclear magnetic resonance (NMR) spectroscopy. It provides a stable and inert environment for dissolving and analyzing samples.

High performance liquid chromatography (hplc) by Shimadzu

Sourced in Japan, United States, Germany, China, Netherlands, Canada, Australia

HPLC (High-Performance Liquid Chromatography) is an analytical technique used to separate, identify, and quantify components in a liquid sample. It utilizes a high-pressure pump to pass the sample mixture through a column packed with a stationary phase, enabling the separation of the components based on their interactions with the stationary and mobile phases.

What are some common applications of DIPEA in chemical synthesis and research?

DIPEA is a versatile organic compound used extensively in a variety of chemical synthesis and research applications. It serves as a non-nucleophilic base, helping to facilitate reactions by assisting with the deprotonation of acidic substrates. DIPEA is particularly valuable in organic chemistry, medicinal chemistry, and materials science, where it is used to form carbon-carbon bonds, protect functional groups, and catalyze important transformations. Its ability to selectively activate and deprotect functional groups makes it a useful reagent for complex molecule synthesis.

How can researchers optimize their use of DIPEA for their projects?

Researchers can leverage the power of AI-driven DIPEA research optimization with PubCompare.ai to effortlessly locate the best protocols from literature, preprints, and patents. The platform's intelligent comparison tools can help you identify the most effective DIPEA protocols for your specific research goals, enabling you to choose the best option for reproducibility and accuracy. PubCompare.ai allows you to screen protocol literature more efficiently and leverage AI to pinpoit critical insights, unleashing your research potential and helping you find the optimal DIPEA solutions for your projects.

Are there any common challenges or considerations when working with DIPEA?

One potential challenge with using DIPEA is its sensitivity to moisture and air. DIPEA is a hygroscopic compound, meaning it readily absorbs water from the atmosphere. This can impact its reactivity and effectiveness in some applications. It's important to handle DIPEA under anhydrous conditions and store it properly to maintain its potency. Additionally, DIPEA is a volatile tertiary amine, so precautions should be taken to avoid inhalation or skin contact during use. Proper personal protective equipment and ventilation are recommended when working with this chemical.

Are there different variations or types of DIPEA that researchers should be aware of?

While DIPEA (N,N-Diisopropylethylamine) is the most common and widely used form, there are some other variations of this tertiary amine that researchers may encounter. For example, there is also N,N-Diethylisopropylamine (DEIPA), which is a similar non-nucleophilic base with slightly different sterric and electronic properties. Researchers should be aware of these structural analogs and how they may perform differently in certain reactions or applications. It's important to carefully select the appropriate DIPEA-like reagent for the specific needs of your research project.

How can PubCompare.ai help researchers find the best DIPEA protocols for their work?

PubCompare.ai allows researchers to more efficiently screen protocol literature and leverage AI to pinpoint critical insights that can help identify the most effective DIPEA protocols for their specific research goals. The platform's intelligent comparison tools can highlight key differences in protocol effectiveness, enabling you to choose the best option for reproducibility and accuracy. By unleashing the power of AI-driven DIPEA research optimization, PubCompare.ai helps researchers find the optimal DIPEA solutions for their projects and experienece the future of research today.

More about "DIPEA"

N,N-Diisopropylethylamine (DIPEA) is a versatile organic compound widely used in chemical synthesis and research.
This tertiary amine serves as a non-nucleophilic base, aiding in various reactions and assisting with the deprotonation of acidic substrates.
DIPEA is particularly valuable in the fields of organic chemistry, medicinal chemistry, and materials science, where it helps facilitate the formation of carbon-carbon bonds, protect functional groups, and catalyze important transformations.
Researchers can leverage the power of AI-driven DIPEA research optimization with PubCompare.ai to effortlessly locate the best protocols from literature, preprints, and patents, unleashing their research potential and finding the optimal DIPEA solutions for their projects.
PubCompare.ai's intelligent comparison tools can help researchers discover the most effective DIPEA-based protocols, from common applications like Millex-LCR filters and HPLC columns (e.g., 21.2×250 mm Luna Axia C18, XB-C18) to more specialized uses in organic synthesis and DMSO-based reactions.
By incorporating DIPEA and related terms like N,N-diisopropylethylamine, piperidine, and CDCl3, researchers can access a wealth of information to optimize their experiments and find the optimal DIPEA-based solutions for their projects.
Experienece the future of research today with PubCompare.ai and unlock the full potential of DIPEA in your work.