Combiflash system

Manufactured by Teledyne

Sourced in United States

The Combiflash system is a flash chromatography instrument used for the purification of organic compounds. It automates the process of separating and isolating desired components from complex mixtures. The Combiflash system operates by utilizing a combination of liquid chromatography and UV detection to efficiently purify samples.

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Lab products found in correlation

Luna c18 column, by Phenomenex (2 mentions) Mercury 400, by Agilent Technologies (1 mentions) Spd m20a, by Shimadzu (1 mentions) Microflex maldi tof instrument, by Bruker (1 mentions) Avance 3 500 mhz, by Bruker (1 mentions) Prominence lc, by Shimadzu (1 mentions) Lc 20ab pump, by Shimadzu (1 mentions) Sil 20a ht, by Shimadzu (1 mentions) Ascend 700 mhz, by Bruker (1 mentions) Mnova software, by Mestrelab Research (1 mentions) Impact 2 q tof mass spectrometer, by Bruker (1 mentions) Av500 instrument, by Bruker (1 mentions) Cms l ms, by Advion (1 mentions) Agilent 1260 series hplc system, by Agilent Technologies (1 mentions) Agilent 1260 series system, by Agilent Technologies (1 mentions) 4800 maldi tof tof ms, by AB Sciex (1 mentions) Lc ms system, by Agilent Technologies (1 mentions) Avance 2 nmr spectrometer, by Bruker (1 mentions) 6230 tofms, by Agilent Technologies (1 mentions) Biflex 4, by Bruker (1 mentions)

Spelling variants of this product

CombiFlash Rf system (32 citations) CombiFlash (26 citations) CombiFlash Rf 200 system (6 citations) CombiFlash Rf flash chromatography system (4 citations) CombiFlash Companion system (3 citations) CombiFlash® EZ Prep system (3 citations) CombiFlash® Rf 200i system (3 citations) CombiFlash Rf+ Lumen chromatography system (3 citations) Combiflash Companion purification system (2 citations) CombiFlash NextGen 300 system (2 citations)

32 protocols using combiflash system

Synthesis of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-b]pyridazine

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To a solution of
3-bromopyrazolo[1,5-b]pyridazine (100 mg, 0.50 mmol)
in 1,4-dioxane (1 mL) were added bis(pinacolato)diboron (141 mg, 0.56
mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II),
complex with CH₂Cl₂ (21 mg, 0.03 mmol), and
potassium acetate (99 mg, 1.01 mmol). The reaction mixture was heated
to 90 °C and stirred for 16 h. The reaction mixture was filtered
through celite and concentrated under reduced pressure. The crude
was purified using flash silica column chromatography on an Isco Combiflash
system (12 g silica, elution with 0–50% EtOAc/petroleum ether
gradient). Desired fractions were combined and concentrated under
reduced pressure. The crude was purified using flash silica column
chromatography on an Isco Combiflash system (12 g silica, elution
with 0–50% 20% MeOH in CH₂Cl₂/CH₂Cl₂ gradient) to afford the title compound, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-b]pyridazine, 92, as a white crystalline solid
(30 mg, 0.12 mmol, 23% yield). R_f 0.38 (EtOAc/petroleum ether 1:1); mp 160–162 °C; ¹H NMR (500 MHz, DMSO-d₆) δ_H 8.53 (dd, J = 4.4, 1.9 Hz, 1H), 8.27 (dd, J = 9.0, 1.9 Hz, 1H), 8.23 (s, 1H), 7.34 (dd, J = 9.0, 4.4 Hz, 1H), 1.30 (s, 12H); LC-MS (ESI): calculated for C₁₂H₁₇BN₃O₂ [M + H]⁺ is 246.1, found 246.1 [M + H]⁺.

Henderson S.H., Sorrell F., Bennett J., Fedorov O., Hanley M.T., Godoi P.H., Ruela de Sousa R., Robinson S., Ashall-Kelly A., Hopkins Navratilova I., Walter D.S., Elkins J.M, & Ward S.E. (2021). Discovery and Characterization of Selective and Ligand-Efficient DYRK Inhibitors. Journal of Medicinal Chemistry, 64(15), 11709-11728.

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Synthesis of SPDP-functionalized NAC

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We added a drop-wise addition of a solution of N-acetyl cysteine (NAC, 5.74 g, 35.24 mmol, 1.1 eq) dissolved in THF (30 mL) to a stirring solution of N-succinimidyl 3-(2-pyridyldithio)-propionate (SPDP) (10 g, 32.04 mmol) in anhydrous tetrahydrofuran (THF, 30 mL) under inert atmosphere. The reaction mixture turned yellow within a few minutes. The reaction mixture was stirred at RT for 2 h. Upon completion, the crude product was purified using pre-packaged high performance redisep gold Rf™ 80-gram silica cartridge on CombiFlash system from Teledyne (Lincoln, NE) keeping the flow at 60 mL/minute. The pure desired product was collected in 4% MeOH in dichloromethane as a white powder with a 75.4% yield (8.8 g).
¹H NMR (500 MHz, CDCl₃): δ 6.67 (d, J = 6.9 Hz, 1H), 4.87 (d, J = 5.5 Hz, 1H), 3.31 (ddd, J = 48.8, 14.2, 4.7 Hz, 2H), 3.13 - 2.99 (m, 4H), 2.88 (s, 4H), 2.09 (s, 3H).¹³C NMR (126 MHz, CDCl₃) δ 171.9, 171.2, 167.0, 52.0, 40.0, 32.8, 31.1, 25.5, 22.9.

Sharma A., Liaw K., Sharma R., Zhang Z., Kannan S, & Kannan R.M. (2018). Targeting Mitochondrial Dysfunction and Oxidative Stress in Activated Microglia using Dendrimer-Based Therapeutics. Theranostics, 8(20), 5529-5547.

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Synthetic Organic Chemistry Protocols

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All of the reagents and solvents
were obtained via commercial sources and used without further purification,
unless otherwise stated. All anhydrous reactions were carried out
under a nitrogen atmosphere. Reactions were monitored by thin-layer
chromatography (TLC) on glass TLC plates with silica gel coated with
fluorescent indicator F254. UV light and TLC stains, including ninhydrin
and 2,4-dinitrophenylhydrazine, were used as visualizing agents. Individual
intermediates and final compounds were purified by flash column chromatography
using an automated Teledyne CombiFlash system (RF + UV–vis).
All ¹H and ¹³C nuclear magnetic resonance (NMR)
spectra were obtained on a Varian Mercury 400, 400 MR, or Varian VNMRS-600
spectrometer at ambient temperature. All target compounds were found
to be ≥95% pure based on analytical high-performance liquid
chromatography analysis. The purities were determined on a Shimadzu
LC-20AP system equipped with an SPD-M21A PDA detector set to λ
= 254 nm and a Phenomenex C18 (250 × 3.9 mm) column. The analyses
were carried out using acetonitrile with 0.1% trifluoroacetic acid
(v/v) in the isocratic mode at a flow rate of 1.8 mL/ min for 14 min.
The injection peak at ∼2 min was excluded in the quantification
of all compounds. The area % of the major peak is ≥95% with
respect to the sum of the area % of other detected peaks.

Ngo C., Fried W., Aliyari S., Feng J., Qin C., Zhang S., Yang H., Shanaa J., Feng P., Cheng G., Chen X.S, & Zhang C. (2023). Alkyne as a Latent Warhead to Covalently Target SARS-CoV-2 Main Protease. Journal of Medicinal Chemistry, 66(17), 12237-12248.

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Isolation and Purification of Toosendanin

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Crude extract (7.033 g) was fractionated stepwise using a Teledyne Isco Combiflash system with a DIOL cartridge. Fraction C, 283.2 mg, eluted with 5:1 ethyl acetate/methanol and was the only active fraction. The Combiflash system was next used with a C18 cartridge, acetonitrile/water gradient (5% acetonitrile for 2 column volumes (CV), then a linear gradient from 5%–100% over 10 CV), and UV 280 nm/time-based fraction collection to further separate 132.1 mg of the active fraction. The resulting active fraction (12.8 mg) corresponded to a low UV active portion of the chromatogram eluting across 70%–80% acetonitrile in water. RP-HPLC using a C18 Luna Phenomenex column (150 × 10 mm, 5 μm particle size, 100Å pore size), time-based collection with one minute increments, and an acetonitrile/water gradient (5 ml/min 30% acetonitrile/water/10 min, linear gradient to 55% at 40 min, linear gradient to 100% at 45 min) was used to purify 2.9 mg of toosendanin from 9.9 mg of the parent fraction.

Long S.A., Huang S., Kambala A., Ren L., Wilson J., Goetz M., Hao X., Yang X., Goncharova E.I., Jia L., LeBlanc A., Khanna C., Henrich C.J, & Beutler J.A. (2020). Identification of potential modulators of osteosarcoma metastasis by high-throughput cellular screening of natural products. Chemical biology & drug design, 97(1), 77-86.

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Purification and Characterization of Organic Compounds

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All chemicals and reagents were purchased from Sigma-Aldrich, Fisher, Aces Pharma, AmBeed, or AA Blocks and used without further purification. Flash chromatography was performed using a Teledyne CombiFlash system using prepackaged silica cartridges from Teledyne. All reactions were run under inert atmosphere unless otherwise noted. RP-HPLC was performed with a Shimadzu LC-20AB pump, Shimadzu SIL-20A HT auto sampler, and Shimadzu SPD-M20A diode array detector using Shimadzu Prominence LC. RP-HPLC was performed using a Luna^® C18 column (5μM, 250mm x 10 mm) (Phenomenex) with product eluting from a mixture of solvent A (water, 0.1 % TFA) and solvent B (acetonitrile, 0.1% TFA). TLC analysis was performed on aluminum backed 60 F₂₅₄ silica sheets from Sigma Aldrich. NMR spectra were recorded on a Bruker Ascend 700 MHz, Bruker Avance III 500 MHz, or Bruker Nanobay 400 MHz spectrometers and referenced to deuterated solvent peak. NMR spectra were processed using Mestrelab Research’s Mnova software (Santiago de Compostela, Spain). ESI-MS was performed on an Aligent 6110 single quad mass spectrometer, HRMS was performed on a Bruker Impact II QTOF mass spectrometer, and MALDI mass spectrometry was performed on a Bruker Microflex MALDI-TOF instrument. All final compounds were purified to >95% as assessed by HPLC with UV detection at λ= 213 and 353 nm.

Cifone M.T., He Y., Basu R., Wang N., Davoodi S., Spagnuolo L.A., Si Y., Daryaee T., Stivala C.E., Walker S.G, & Tonge P.J. (2022). Heterobivalent Inhibitors of Acetyl-CoA Carboxylase: Drug Target Residence Time and Time-Dependent Antibacterial Activity. Journal of medicinal chemistry, 65(24), 16510-16525.

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Isolation and Characterization of Fungal Metabolites

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A. nidulans harboring mps genes were grown in CD-ST for 5 days and then extracted with ethyl acetate twice. The organic phase was dried by speed Vacuum and dissolved in methanol for analysis. LC–MS analyses were performed on Thermo Scientific U3000/LCQ Fleet with Phenomenex Luna C18 column (3 μm, 2.0 × 150 mm). LC analyses were achieved with a linear gradient of 5–95% CH₃CN-H₂O in 30 min followed by 95% CH₃CN for 5 min with a flow rate of 0.25 ml/min. For isolation of compounds, ethyl acetate extract from 10 L culture was evaporated by Buchi Rotavapor and the crude extracts were injected to Combi-Flash system (Teledyne Isco) with a reversed-phase C18 column for initial separation. Fractions containing the target compounds were used for further purification by HPLC with a C18 column of Phenomenex Luna (5 μm, 10 × 250 mm). 1D and 2D NMR spectra were obtained on Bruker AVANCE III HD 600 MHz NMR spectrometer to elucidate the chemical structures of compounds.

Yu C., Chen L., Gao Y.L., Liu J., Li P.L., Zhang M.L., Li Q., Zhang H.D., Tang M.C, & Li L. (2022). Discovery and biosynthesis of macrophasetins from the plant pathogen fungus Macrophomina phaseolina. Frontiers in Microbiology, 13, 1056392.

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Automated Synthesis of Peptides

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The reagents and solvents were purchased from commercial sources (Fisher) and used directly. The intermediates and products were purified by using an ISCO CombiFlash system and prepacked SiO₂ cartridges. Final compounds were purified on preparative high-pressure liquid chromatography (RP-HPLC) was performed on Agilent 1260 Series system. Systems were run with 0–20% methanol/water gradient with 0.1% TFA. NMR spectra were acquired on a Bruker AV500 instrument (500 MHz for ¹H-NMR, 126 MHz for ¹³C-NMR). TLC-MS were acquired using Advion CMS-L MS. Matrix-assisted laser desorption ionization mass spectra (MALDI-MS) data were acquired in positive-ion mode using a Sciex 4800 MALDI TOF/TOF MS. The peptides were synthesized using a CEM Liberty Blue Automated Microwave Peptide Synthesizer with the manufacturers standard coupling cycles at 0.1 mmol scale. The purity of final compounds was confirmed by Waters LC-MS system and/or Agilent 1260 Series HPLC system. Systems were run with 0–40% methanol/water gradient with 0.1% TFA. All the purity of target compounds showed >95% in RP-HPLC.

Chen D., Dong C., Dong G., Srinivasan K., Min J., Noinaj N, & Huang R. (2020). Probing the Plasticity in the Active Site of Protein N-terminal Methyltransferase 1 Using Bisubstrate Analogs. Journal of medicinal chemistry, 63(15), 8419-8431.

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Bromination of Methyloxazole Carboxylate

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To a round-bottom flask were added methyl 5-methyloxazole-4-carboxylate (3.54 mmol) and THF (17.7 mL). The mixture was cooled to −78 °C, and then lithium bis(trimethylsilyl)amide (5.32 mmol) was added dropwise. The mixture was allowed to stir at −78 °C for 15 min, and then bromine (7.03 mmol) was added dropwise. The mixture was allowed to stir for 1 h at −78 °C. Upon completion, as determined by LCMS, the mixture was allowed to warm to rt, and the reaction was quenched with satd NaS₂O₃, diluted with brine, and extracted with DCM. The organics were dried with Na₂SO₄ and then filtered and concentrated to dryness. The sample was purified via Teledyne ISCO Combi-Flash system (solid loading, 40G column, 0–30% EtOAc, 25 min run) to afford 190.6 mg (25% yield) of the desired product as an off-white solid. ¹H NMR (400 MHz, CDCl₃): δ 3.90 (s, 3H), 2.63 (s, 3H). ¹³C{¹H} NMR (100 MHz, CDCl₃): 161.6, 160.1, 132.0, 130.0, 52.3, 12.1. LCMS: t_R = 0.623 min (>98%); m/z = 222.0 [M + H]⁺. HRMS (TOF, ES+): C₆H₇BrNO₃ [M + H]⁺ calcd mass 219.9609, found 219.9604. Mp: 78.4–81.1 °C.

Childress E.S., Garrison A.T., Sheldon J.R., Skaar E.P, & Lindsley C.W. (2019). Total Synthesis of Hinduchelins A–D, Stereochemical Revision of Hinduchelin A, and Biological Evaluation of Natural and Unnatural Analogues. The Journal of organic chemistry, 84(10), 6459-6464.

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Palladium-Catalyzed Borylation of Oxazole

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To a round-bottom flask were added boronic acid (0.30 mmol), methyl 2-bromo-5-methyl-oxazole-4-carboxylate (0.27 mmol), tetrakis(triphenylphosphine)palladium(0) (0.03 mmol), and potassium carbonate, 0.33 mmol) in 1,4-dioxane (3.4 mL) and water (1.1 mL). The reaction flask was purged with nitrogen for 5 min, and then the reaction was stirred for 4 h at 90 °C. Upon completion, as determined by LCMS, the reaction was cooled to rt, and then solvent was removed in vacuo. The crude solid was taken up in DCM, syringe filtered and then purified via Teledyne ISCO Combi-Flash system (solid loading, 40G column, 10–60% EtOAc, 25 min run) to afford pure products.

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Synthesis of Piperidine-Containing Compound

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Example 7

A mixture of INTERMEDIATE a7 (80 mg, 0.253 mmol), 2-(piperidin-2-yl)ethanol (65.5 mg, 0.507 mmol), and N-ethyl-N-isopropylpropan-2-amine (131 mg, 1.013 mmol) in ethanol (3 mL) was stirred at room temperature for 36 h and then at 50° C. for 6 h.

For work-up, the reaction mixture was extracted with H₂O/CH₂Cl₂, and the combined organic layers were washed with brine, dried over MgSO₄, filtered, and concentrated. The resultant residue was chromatographically purified using a Teledyne Isco CombiFlash® system (normal phase: 4 g column, eluent: 3-5% CH₃OH/CH₂Cl₂). The material obtained from the chromatography was triturated with ethyl acetate/diisopropyl ether, and the resultant solid was collected by filtration and dried in a vacuum oven overnight to give the titled compound as a white solid (15 mg, 15.0%). LC-MS (ESI+) m/z 409.4 [M+H]+; ¹H NMR (600 MHz, DMSO-d₆) δ ppm 6.22 (s, 1H), 6.07 (s, 1H), 5.05 (s, 1H), 4.67 (dd, J=6.0, 4.7 Hz, 1H), 3.90 (d, J=13.0 Hz, 1H), 3.46-3.35 (m, 2H), 3.35-3.21 (m, 3H), 2.44 (s, 2H), 2.37 (s, 3H), 1.93-1.83 (m, 4H), 1.83-1.58 (m, 11H), 1.57-1.49 (m, 9H).

US10155770B2. Substituted pyrazolopyrimidines and method of use (2018-12-18). AbbVie Deutschland GmbH & Co. KG [DE], AbbVie Inc. [US]. Inventors: Ramin Faghih [US], Achim Moeller [DE], Michael Ochse [DE], Frauke Pohlki [DE], Martin Schmidt [DE], Kevin Sippy [US], Sean Turner [DE], Elizabeth Louise Van Der Kam [DE].

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