All reagents were used
as received from commercial sources unless otherwise noted. 1H and 13C spectra were obtained in DMSO-d6 or CDCl3 at room temperature, unless otherwise
noted, on Varian Inova 400 MHz, Varian Inova 500 MHz, Bruker Avance
DRX 500, or Bruker Avance DPX 300 instrument. Chemical shifts for
the 1H NMR and 13C NMR spectra were recorded
in parts per million (ppm) on the δ scale from an internal standard
of residual tetramethylsilane (0 ppm). Rotamers are described as a
ratio of rotamer A to rotamer B if possible. Otherwise, if the rotamers
cannot be distinguished, the NMR peaks are described as multiplets.
Mass spectrometry data were obtained on a Waters Corporation LCT.
Purity of all tested compounds was assessed by HPLC using an Agilent
1100 series with an Agilent Zorbax Eclipse Plus C18 column (254 nm
detection) with the following gradient: 10% ACN/water (1 min), 10–90%
ACN/water (6 min), and 90% ACN/water (2 min). Values for each compound
are included at the end of each experimental procedure, and all are
over 95% pure. HPLC retention times (tR) were recorded in minutes (min). Solvent abbreviations used are
the following: MeOH (methanol), DCM (dichloromethane), EtOAc (ethyl
acetate), Hex (hexanes), DMSO (dimethylsulfoxide), DMF (dimethylformamide),
H2O (water), THF (tetrahydrofuran), ACN (acetonitrile).
Reagent abbreviations used are the following: HATU (O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium
hexafluorophosphate), HOAT (1-hydroxy-7-azabenzotriazole), HOBt (1-hydroxy-1,2,3-benzotriazole),
EDCI (N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride), DIEA (diisopropylethylamine),
TFA (trifluoroacetic acid), MgSO4 (magnesium sulfate),
Na2SO4 (sodium sulfate), NaHCO3 (sodium
bicarbonate), Na2CO3 (sodium carbonate), Cs2CO3 (cesium carbonate), NH4Cl (ammonium
chloride), K2CO3 (potassium carbonate), KOH
(potassium hydroxide), HCl (hydrogen chloride), NaOH (sodium hydroxide),
LiOH (lithium hydroxide), LAH (lithium aluminum hydride), EtOH (ethanol),
NaCN (sodium cyanide), Et2O (diethyl ether), CsF (cesium
fluoride), NaCl (sodium chloride), TBSCl (tert-butyldimethylsilyl
chloride), Ms2O (methanesulfonic anhydride), MsCl (methanesulfonyl
chloride), AcOH (acetic acid), NaBH4 (sodium borohydride),
NaBH3CN (sodium cyanoborohydride), H2 (hydrogen),
N2 (nitrogen), MS (molecular sieves). Assay abbreviations
are the following: LUC (luciferase), MTT ((3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium
bromide. Additional abbreviations are the following: aq (aqueous),
saturated (saturated), rt (room temperature). All anhydrous reactions
were run under an atmosphere of dry nitrogen.
as received from commercial sources unless otherwise noted. 1H and 13C spectra were obtained in DMSO-d6 or CDCl3 at room temperature, unless otherwise
noted, on Varian Inova 400 MHz, Varian Inova 500 MHz, Bruker Avance
DRX 500, or Bruker Avance DPX 300 instrument. Chemical shifts for
the 1H NMR and 13C NMR spectra were recorded
in parts per million (ppm) on the δ scale from an internal standard
of residual tetramethylsilane (0 ppm). Rotamers are described as a
ratio of rotamer A to rotamer B if possible. Otherwise, if the rotamers
cannot be distinguished, the NMR peaks are described as multiplets.
Mass spectrometry data were obtained on a Waters Corporation LCT.
Purity of all tested compounds was assessed by HPLC using an Agilent
1100 series with an Agilent Zorbax Eclipse Plus C18 column (254 nm
detection) with the following gradient: 10% ACN/water (1 min), 10–90%
ACN/water (6 min), and 90% ACN/water (2 min). Values for each compound
are included at the end of each experimental procedure, and all are
over 95% pure. HPLC retention times (tR) were recorded in minutes (min). Solvent abbreviations used are
the following: MeOH (methanol), DCM (dichloromethane), EtOAc (ethyl
acetate), Hex (hexanes), DMSO (dimethylsulfoxide), DMF (dimethylformamide),
H2O (water), THF (tetrahydrofuran), ACN (acetonitrile).
Reagent abbreviations used are the following: HATU (O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium
hexafluorophosphate), HOAT (1-hydroxy-7-azabenzotriazole), HOBt (1-hydroxy-1,2,3-benzotriazole),
EDCI (N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride), DIEA (diisopropylethylamine),
TFA (trifluoroacetic acid), MgSO4 (magnesium sulfate),
Na2SO4 (sodium sulfate), NaHCO3 (sodium
bicarbonate), Na2CO3 (sodium carbonate), Cs2CO3 (cesium carbonate), NH4Cl (ammonium
chloride), K2CO3 (potassium carbonate), KOH
(potassium hydroxide), HCl (hydrogen chloride), NaOH (sodium hydroxide),
LiOH (lithium hydroxide), LAH (lithium aluminum hydride), EtOH (ethanol),
NaCN (sodium cyanide), Et2O (diethyl ether), CsF (cesium
fluoride), NaCl (sodium chloride), TBSCl (tert-butyldimethylsilyl
chloride), Ms2O (methanesulfonic anhydride), MsCl (methanesulfonyl
chloride), AcOH (acetic acid), NaBH4 (sodium borohydride),
NaBH3CN (sodium cyanoborohydride), H2 (hydrogen),
N2 (nitrogen), MS (molecular sieves). Assay abbreviations
are the following: LUC (luciferase), MTT ((3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium
bromide. Additional abbreviations are the following: aq (aqueous),
saturated (saturated), rt (room temperature). All anhydrous reactions
were run under an atmosphere of dry nitrogen.
