PMC:7571312 / 35060-37077 JSONTXT

{"target":"https://pubannotation.org/docs/sourcedb/PMC/sourceid/7571312","sourcedb":"PMC","sourceid":"7571312","source_url":"https://www.ncbi.nlm.nih.gov/pmc/7571312","text":"Unless otherwise noted, materials were obtained from commercial suppliers and used without further purification. The removal of solvent under reduced pressure or concentration refers to distillation using a Büchi rotary evaporator attached to a vacuum pump (3 mmHg). Products obtained as solids or high-boiling oils were dried under vacuum (1 mmHg). Silica gel chromatography was performed on either a CombiFlash (Teledyne ISCO), SP4, or Isolera (Biotage) purification system. All reactions were performed under a positive pressure of nitrogen or argon or with a drying tube at an ambient temperature (unless otherwise stated) in anhydrous solvents, unless otherwise indicated. Analytical thin-layer chromatography (TLC) was performed on glass-backed silica gel 60 F254 plates (Analtech, 0.25 mm), eluting with the appropriate solvent ratio (v/v). The reactions were assayed by high-performance liquid chromatography–mass spectrometry (LCMS) or TLC and terminated as judged by the consumption of the starting material. LCMS utilized wavelengths of 254 and 220 nm and either electrospray ionization (ESI) in positive mode or atmospheric-pressure chemical ionization (APCI) in positive mode. The TLC plates were visualized using UV light, p-anisaldehyde, phosphomolybdic acid, or iodine staining. Microwave-assisted reactions were run in a Biotage Initiator. 1H NMR spectra were recorded on a Bruker XWIN-NMR (400 MHz) spectrometer. Proton chemical shifts are reported in parts per million downfield from tetramethylsilane (TMS). 1H NMR data are reported as chemical shift (multiplicity, coupling constant, integration). Multiplicities are denoted as follows: s, singlet; d, doublet; t, triplet; q, quartet; dd, doublet of doublets; dt, doublet of triplets; and brs, broad singlet. For spectra obtained in CDCl3, DMSO-d6, and CD3OD, the residual protons (7.27, 2.50, and 3.31 ppm, respectively) were used as the internal references. The purity of the final products is \u003e95% as determined by HPLC and/or 1H NMR 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