All the solvent and chemicals were purchased from Sigma Aldrich, Alfa Aesar, Acros Organic and FluoroChem and were used without further purification. All air sensitive reactions were carried out under an argon or nitrogen atmosphere. Thin‐layer chromatography (TLC) was performed on pre‐coated aluminium sheets of Merck silica gel 60 F254 (0.20 mm) and visualised by UV radiation (254 nm). Automated column chromatography was performed on a Biotage® Isolera Four. 1H NMR and 13C NMR spectra were measured on Bruker DPX 300, 400 or 500 apparatus. Mass spectrometric measurements were performed by the EPSRC Mass Spectrometry Facility in Swansea University on a Waters Xevo G2‐S and on a Thermo Scientific LTQ Orbitrap XL machine for high‐resolution mass spectroscopy (HRMS). The electrochemical reactions were carried out in a galvanostatic mode using a GWINSTEK GPR‐30H10D.
Isolera four
Manufactured by Biotage
Sourced in Sweden
The Isolera Four is a laboratory instrument designed for automated flash chromatography. It is capable of performing purification and isolation of compounds from complex mixtures. The Isolera Four utilizes UV-Vis detection for monitoring and collecting fractions during the purification process.
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Lab products found in correlation
Ltq orbitrap xl, by Thermo Fisher Scientific (2 mentions)
Tlc silica gel 60 f254 plate, by Merck Group (2 mentions)
Avance 3 600 mhz spectrometer, by Bruker (1 mentions)
Xevo tq s, by Waters Corporation (1 mentions)
Dd2 400 mhz nmr, by Agilent Technologies (1 mentions)
Dd2 600 mhz nmr spectrometer, by Agilent Technologies (1 mentions)
Zorbax 300sb c18, by Agilent Technologies (1 mentions)
Acidic, by Waters Corporation (1 mentions)
Sunfire prep c18, by Waters Corporation (1 mentions)
Zorbax 300sb c18 column, by Agilent Technologies (1 mentions)
Zorbax 300sb c18 semi preparative column, by Agilent Technologies (1 mentions)
Gemini nx c18, by Phenomenex (1 mentions)
Lichroprep rp 18, by Merck Group (1 mentions)
9 protocols using isolera four
1
Electrochemical Synthesis of Organic Compounds
2
Purification and Characterization of GAA
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Unless otherwise stated, all reagents and solvents were obtained from commercial sources were used without further purification. GAA were purchased from Biopurify (Chengdu, China). Flash column chromatography was performed on Biotage Isolera Four (Sweden). 1H NMR and 13C-APT spectra were recorded on a Bruker AvanceIII 600MHz spectrometer (Germany). HRMS was performed on a Thermo Fisher LTQ Orbitrap XL (United States).
3
Synthesis and Characterization of Novel Compounds
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All chemicals were purchased from commercial suppliers and used without further purification. NMR spectra of all synthesized compounds were carried out on an Agilent DD2-400 MHz NMR or Agilent DD2-600 MHz NMR spectrometer with ProbeOne. All chemical shifts of 1H and 13C signals were reported in parts per million using TMS as internal standard at 25 °C and all spectra were calibrated using the respective solvent signal. Mass spectra were recorded on an Advion ExpressIon CMS or Xevo T-QS (Waters) using electrospray ionization. TLC analyses for reaction control were performed on Merck Silica Gel 60 F254 TLC plates and visualized using UV light. Analytical HPLC was performed on VWR Hitachi with an Agilent C18 column (Agilent Zorbax 300SB-C18, 100 mm × 4.6 mm) and acetonitrile/water (0.1% TFA each) as mobile phase. Chromatographic separations were performed using automated flash column chromatography on Isolera Four (Biotage) using silica gel cartridges (SNAP KP-Sil; 10 g or 25 g) and reversed phase HPLC system Knauer Azura with Zorbax 300SB-C18 semi-preparative column and acetonitrile/water (0.1% TFA each) as mobile phase. Starting materials such as anhydrous solvents, dimethyl 4-hydroxypyridine-2,6-dicarboxylate (TCI Europe) and 4,13-diaza-18-crown-6 (Merck) were purchased and used as received. Methyl 6-(chloromethyl)picolinate was prepared according to the literature [44 (link)].
4
Synthesis of Pyrimidin-2-yl Picolinate Derivative
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Example 84
To a solution of lithium 6-methyl-3-(pyrimidin-2-yl)picolinate [prepared as described in WO 2012/089607] (29 mg, 0.13 mmol), Intermediate 31 (32 mg, 0.13 mmol) and HATU (54 mg, 0.14 mmol) in DMF (5 mL) at 0° C. was added DIPEA (62 μL, 0.36 mmol) and the reaction mixture was allowed to warm to ambient temperature and stirred for 88 hrs. The mixture was diluted with EtOAc (30 mL) and washed with saturated aqueous NaHCO3. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on the Biotage Isolera Four™ (10 g column, 1 to 10% methanol in DCM). The crude product was further purified by preparative HPLC (Gilson, Acidic (0.1% Formic acid), Waters Sunfire Prep-C18, 10 μm, 30×100 mm column, 10 to 95% MeCN in Water) and lyophilised from 10% MeCN in water (3 mL) to give the title compound as a solid (39 mg)
LCMS (Method I): 3.30 min, 446 [M+H]+
1H NMR (500 MHz, DMSO-d6) 9.11 (d, 1.2 H), 9.09 (d, 0.8 H), 8.87 (s, 0.4 H), 8.82 (s, 0.4 H), 8.71 (s, 0.6 H), 8.67 (s, 0.6 H), 8.64-8.62 (d, 0.4 H), 8.62-8.59 (d, 0.6 H), 8.49 (bm, 0.6 H), 8.02 (t, 0.4 H), 7.66 (m, 1 H), 7.62 (m, 1 H), 4.84 (m, 0.4 H), 3.98 (m, 0.6 H), 3.87-3.75 (m, 1 H), 3.75-3.66 (m, 1 H), 3.06 (s, 1.8 H), 2.92 (s, 1.2 H), 2.72 (s, 1.8 H), 2.70 (s, 1.2 H), 1.80 (m, 2 H), 1.20 (t, 1.2 H), 1.03 (t, 1.8 H).
5
Electrochemical Oxidation of Organic Substrates
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The substrate (0.35 mmol, 1 equiv), TEMPO (0.53 mmol, 1.5 equiv), Bu4NBF4 (1.0 mmol), Na2CO3 (0.39 mmol, 1.1 equiv) were placed in a 25 mL three‐necked round‐bottom flask equipped with a RVC anode and a platinum wire cathode. The flask was flushed with argon. Acetonitrile (9.5 mL) and water (0.5 mL) were added. The resulting mixture was sonicated for 0.5 min. The electrolysis was carried out at 60 °C and a constant current of 10 mA until complete consumption of the substrate (monitored by TLC or 1H NMR). The reaction mixture was cooled to RT. Water (25 mL) and ethyl acetate (25 mL) were added. The phases were separated and the aqueous phase was extracted with ethyl acetate (2×25 mL). The combined organic solution was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was chromatographed through silica gel eluting with ethyl acetate/hexanes to give the product. Automated column chromatography was also performed on a Biotage® Isolera Four for purification of few products.
6
Synthesis and Characterization of Novel Compounds
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All chemicals were purchased from commercial suppliers and used without further purification. Mass spectra (MALDI-MS) were recorded on a Bruker Autoflex Max MALDI/TOF-MS/MS system (Bruker, Bremen, Germany). TLC analyses for reaction control were performed on Merck Silica Gel 60 F254 TLC plates and visualized using 254 nm UV light. HPLC was performed on VWR Hitachi using analytical Zorbax 300SB-C18 column, 100 × 4.6 mm (Agilent Technologies, Waldbronn, Germany) and acetonitrile/water (0.1% TFA each) as mobile phase using a flow rate of 1 mL/min. Chromatographic separations were performed using automated flash column chromatography on Isolera Four (Biotage, Uppsala, Sweden) using silica gel cartridges (SNAP HC-Sfär; 5 g, 10 g, or 25 g) and reversed phase HPLC system Knauer Azura (Knauer, Berlin, Germany) with Zorbax 300SB-C18 semi-preparative column (Agilent Technologies, Waldbronn, Germany) and acetonitrile/water (0.1% TFA each) as mobile phase using a flow rate of 6 mL/min. Compound 1 as well as mcp-M-click and mcp-D-click were synthesized in accordance to the literature 25 (link).
7
Inert Atmosphere Synthesis Protocols
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All moisture and air sensitive reactions were carried out in oven dried flasks under an inert argon atmosphere. RT refers to 25 °C maintained by the use of a heating mantle. All reactions were covered with foil unless otherwise stated and were magnetically stirred. Merck Geduran® Si 60 silica gel or Biotage® Isolera™ four with either Biotage® SNAP/SNAP Ultra cartridges (10 g, 20 g, 50 g or 100 g) were used for column chromatography during purification. DC Fertigfolien ALUGRAM aluminium sheets coated with silica gel, were used for carrying out analytical thin layer chromatography (TLC). Compounds were visualised by ultra-violet light. Chemicals were used as supplied. Anhydrous solvents were supplied commercially and used under an inert argon atmosphere. All other solvents and reagents used were supplied commercially and used as received.
8
Purification and Characterization of Compounds
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Flash chromatography was carried out on a Biotage Isolera Four with self-packed columns. For reverse phase LiChroprep RP-18, 40-63 μM silica (Merck) was used with the indicated solvent system, whereby the gradients were adjusted for the individual compounds based on their UHPLC trace.
Preparative RP-HPLC was performed on a Shimadzu Prominence UFLC Preparative Liquid Chromatograph using a Gemini NX-C18, 5 μm, 110 Å, 21.2 x 250 mm from Phenomenex column with a flow rate of 20 mL/min and the indicated solvent system, whereby the gradients were adjusted for the individual compounds based on their UHPLC trace.
Solvent systems used for RP-flash chromatography and preparative RP-HPLC: NMR: 1 H, 13 C and 2D-NMR were recorded on a BrukerAvance (400 or 500 MHz); in ppm relative to solvent signal; multiplicities in Hz (reported as br = broad signal, s = singlet, d = doublet, t = triplet or a combination of these eg. dd). HRMS: Bruker maXis 4G QTOF ESI mass spectrometer.
Preparative RP-HPLC was performed on a Shimadzu Prominence UFLC Preparative Liquid Chromatograph using a Gemini NX-C18, 5 μm, 110 Å, 21.2 x 250 mm from Phenomenex column with a flow rate of 20 mL/min and the indicated solvent system, whereby the gradients were adjusted for the individual compounds based on their UHPLC trace.
Solvent systems used for RP-flash chromatography and preparative RP-HPLC: NMR: 1 H, 13 C and 2D-NMR were recorded on a BrukerAvance (400 or 500 MHz); in ppm relative to solvent signal; multiplicities in Hz (reported as br = broad signal, s = singlet, d = doublet, t = triplet or a combination of these eg. dd). HRMS: Bruker maXis 4G QTOF ESI mass spectrometer.
9
Purification and Analysis of Compounds
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Semi-preparative RP-HPLC was performed on a Knauer Smartline 1000 HPLC system in combination with a Macherey Nagel VP 250/21 Nucleosil 120-5 C18 column. Conditions were 0-40 min 5-60% B at a flow rate of 12 mL min -1 . Samples were lyophilized using a Christ Alpha 1-2 LD plus lyophilizer. For automated reversed-phase flash chromatography, a Biotage Isolera Four in combination with a SNAP Ultra C18 column (30g) was used. The solvent system was A = H2O (0.1% TFA) and B = acetonitrile (0.1% TFA). UV detection was set to 220 nm and 240 nm.
The gradient used was 0 -30 mL 0% B, 30 -120 mL 0-100% B, 120 -150 mL 100% B at a flow rate of 25 mL min -1 . Radioactivity measurements were made by using an Activimeter ISOMED
The gradient used was 0 -30 mL 0% B, 30 -120 mL 0-100% B, 120 -150 mL 100% B at a flow rate of 25 mL min -1 . Radioactivity measurements were made by using an Activimeter ISOMED
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