Combiflash isco system

Manufactured by Teledyne

The Combiflash ISCO system is a versatile laboratory equipment designed for purification and separation of chemical compounds. It utilizes flash chromatography to efficiently isolate and purify samples. The system provides automated control and monitoring of parameters such as flow rate, pressure, and UV detection to ensure reliable and reproducible results.

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Lab products found in correlation

Universal phase separator, by Biotage (2 mentions) Gx 281, by Gilson (1 mentions) Avance 3, by Bruker (1 mentions)

Spelling variants of this product

Combiflash system (32 citations) CombiFlash (26 citations) Combiflash ISCO (9 citations) ISCO CombiFlash Rf system (5 citations)

6 protocols using combiflash isco system

Synthesis of Trifluoroacetic Acid Derivative

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example 188

Trifluoroacetic acid (1.12 mL, 14.7 mmol) was added to a stirred solution of tert-butyl N-({[(2S)-1-[(2S,4R)-4-hydroxy-2-({[4-(4-methyl-1,3-oxazol-5-yl)phenyl]methyl}carbamoyl)pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl}methyl)-N-[5-(4-{[trans-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]carbamoyl}phenoxy)pentyl]carbamate (34 mg, 0.0327 mmol) in DCM (3.00 ml) at room temperature. The resulting mixture was stirred at 45° C. for 48 h. The reaction mixture was then concentrated under reduced pressure to give a crude material, which was purified by flash silica gel chromatography on a Teledyne Combiflash ISCO system, eluting with MeOH/DCM (gradient: v:v=0:100 to 10:90) to yield the desired title product (yield: 62%).

US11427548B2. Compounds and methods for the targeted degradation of androgen receptor (2022-08-30). Arvinas Operations, Inc. [US]. Inventors: Andrew P. Crew [US], Hanqing Dong [US], Jing Wang [US], Xin Chen [US], Yimin Qian [US], Kurt Zimmermann [US], Michael Berlin [US], Lawrence Snyder [US].

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Synthesis of a Novel Pyrrolidine-Based Compound

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Example 188

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Trifluoroacetic acid (1.12 mL, 14.7 mmol) was added to a stirred solution of tert-butyl N-({[(2S)-1-[(2S,4R)-4-hydroxy-2-({[4-(4-methyl-1,3-oxazol-5-yl)phenyl]methyl}carbamoyl)pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl}methyl)-N-[5-(4-{[trans-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]carbamoyl}phenoxy)pentyl]carbamate (34 mg, 0.0327 mmol) in DCM (3.00 ml) at rt. The resulting mixture was stirred at 45° C. for 48 h. The reaction mixture was then concentrated under reduced pressure to give a crude material, which was purified by flash silica gel chromatography on a Teledyne Combiflash ISCO system, eluting with MeOH/DCM (gradient: v:v=0:100 to 10:90) to yield the desired title product (yield: 62%).

US11352351B2. Compounds and methods for the targeted degradation of androgen receptor (2022-06-07). Arvinas, Inc. [US]. Inventors: Meizhong Jin [US], Andrew P. Crew [US], Hanqing Dong [US], Jing Wang [US], Xin Chen [US], Yimin Qian [US].

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Synthesis of Novel Benzoic Acid Derivative

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Example 172

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TBTU (21.5 mg, 0.067 mmol) was added to a solution of 4-{[5-({[(2S)-1-[(2S,4R)-4-hydroxy-2-({[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl}carbamoyl)pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl}methoxy)pentyl]amino}benzoic acid (31 mg, 0.044 mmol), 2-chloro-4-[trans-3-amino-2,2,4,4-tetramethylcyclobutoxy]benzonitrile (12.4 mg, 0.044 mmol) in DMF (3.0 mL) and DIPEA (15.4 μL, 0.089 mmol) at rt. The resulting reaction mixture was stirred at rt for 1 hr. LC-MS indicated formation of the desired product. The reaction mixture was diluted with EtOAc (30 mL), washed with water (15 mL×2), brine (15 mL×1), filtered through a Biotage universal phase separator and then concentrated under reduced pressure to give a crude residue, which was purified by silica gel chromatography on a Teledyne Combiflash ISCO system eluting with MeOH/DCM (v/v=0:100 to 10:90) to yield the desired title product (yield: 41%).

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Synthesis of Biaryl-Containing Compound

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example 172

TBTU (21.5 mg, 0.067 mmol) was added to a solution of 4-{[5-({[(2S)-1-[(2S,4R)-4-hydroxy-2-({[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl}carbamoyl)pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl}methoxy)pentyl]amino}benzoic acid (31 mg, 0.044 mmol), 2-chloro-4-[trans-3-amino-2,2,4,4-tetramethylcyclobutoxy]benzonitrile (12.4 mg, 0.044 mmol) in DMF (3.0 mL) and DIPEA (15.4 μL, 0.089 mmol) at room temperature. The resulting reaction mixture was stirred at room temperature for 1 hr. LC-MS indicated formation of the desired product. The reaction mixture was diluted with EtOAc (30 mL), washed with water (15 mL×2), brine (15 mL×1), filtered through a Biotage universal phase separator and then concentrated under reduced pressure to give a crude residue, which was purified by silica gel chromatography on a Teledyne Combiflash ISCO system eluting with MeOH/DCM (v/v=0:100 to 10:90) to yield the desired title product (yield: 41%).

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Spectroscopic Analysis of Organic Compounds

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Low pressure flash chromatography was carried out using a Teledyne Isco CombiFlash system. Preparative HPLC was carried out in a Gilson GX281 instrument (Gilson Inc., Middleton, WI, USA). NMR spectra were recorded on a Bruker Avance III spectrometer (500 and 125 MHz for ¹H and ¹³C-NMR, respectively, Bruker, Billerica, MA, USA) equipped with a 1.7-mm TCI MicroCryoProbe™, using the signal of the residual solvent as THE internal reference (^δH 3.31 and ^δC 49.0 ppm for CD₃OD). LC-UV-HRMS analysis was performed as previously described [22 (link),23 (link)]. Two different gradients were used in these analyses, employing the same solvent system. Solvent A consisted of 10% acetonitrile and 90% water with 1.3 mM trifluoroacetic acid and ammonium formate, and Solvent B was 90% acetonitrile and 10% water with 1.3 mM trifluoroacetic acid and ammonium formate. The first gradient started at 10% B and went to 100% B in 6 minutes, was kept at 100% B for 2 min and returned to 10 % B for 2 min to initialize the system. The second gradient started at 1% B and went to 10% B in 6 min, then to 100% B in 0.1 min, was kept at 100% B for 1.9 min and returned to 1 % B for 2 min to initialize the system.

Sekurova O.N., Pérez-Victoria I., Martín J., Degnes K.F., Sletta H., Reyes F, & Zotchev S.B. (2016). New Deferoxamine Glycoconjugates Produced upon Overexpression of Pathway-Specific Regulatory Gene in the Marine Sponge-Derived Streptomyces albus PVA94-07. Molecules, 21(9), 1131.

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Synthesis of Intermediate B from A

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To a solution of intermediate A (1 equiv) in EtOH (0.35 M) was added water (2.8 equiv), followed by hydrazine (7 equiv). The reaction was then heated to 80 °C for 4 h. The reaction was then poured into cold water and concentrated. The crude material was purified on a Teledyne ISCO CombiFlash System by (dry-loading) (EtOAc/DCM: 0–3%) to give intermediate B.

Alverez C.N., Park J.E., Toti K.S., Xia Y., Krausz K.W., Rai G., Bang J.K., Gonzalez F.J., Jacobson K.A, & Lee K.S. (2020). Identification of a New Heterocyclic Scaffold for Inhibitors of the Polo-Box Domain of Polo-like Kinase 1. Journal of medicinal chemistry, 63(22), 14087-14117.

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