5381-20-4,5381-20-4, Thianaphthene-3-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
To a 20-mL sealed tube purged and maintained with an inert atmosphere of nitrogen,was placed a solution of 2-ethyl-5-[(3-methylcyclohexyl)oxyjaniline (1.0 g,4.29 mmol,as prepared in the previous step) in EtOH (10 mL) then 2-oxopropanoic acid (1.13 g,12.83 mmol) and 1-benzothiophene-3-carbaldehyde (626 mg,3.86 mmol) were added. The reaction was stirred overnight at 120C then concentrated under reduced pressure. The crude product was purified by Flash-PrepHPLC (IntelFlash-1: Column,C18; mobile phase,ACN,water (0.5% TFA) and ACN (80.0%ACN up to 95.0% in 15 mm); Detector,UV 254 nm) then the isomers were separated by PrepSFC (Prep 5FC350-2: Column,CHIRALPAK AD-H SFC,5*25cm,Sum; mobile phase,C02(50%),ethanol(2mM NH3-MeOH); Detector,UV 254 nm) affording 56.7 mg (3%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 R,3 S)-3-methylcyclohexylj oxyl quinoline-4-carboxylic acid (Compound 182) as alight yellow solid,53.9 mg(4%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 R,3R)-3-methylcyclohexyll oxyl quinoline-4-carboxylic acid (Compound 184) as a light yellow solid and a mixture of Compound 181 and Compound 183. This mixture was separated by Chiral-Prep-HPLC (HPLC-09: Column: CHIRALPAK-AD-H-5L002,20*250 mm; Mobile Phase A:Hex–HPLC,Mobile Phase B: IPA–HPLC; Flow rate: 15 mL/min; Gradient: 40 B to 40 B in 16 mm; 254 nm) affording 55.7 mg (3%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 S,3R)-3-methylcyclohexyll oxyl quinoline-4-carboxylic acid (Compound 181) as a brown solid and 56.8 mg (3%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 S,35)-3-methylcyclohexyljoxyjquinoline-4-carboxylic acid (Compound 183) as a brown solid. j0401j 2-(1-Benzothiophen-3-yl)-8-ethyl-5-j j(1S,3R)-3-methylcyclohexyljoxyjquinoline-4-carboxylic acid (Compound 181): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (brs,1H ),9.26 (d,J= 7.5 Hz,1H ),8.81 (s,1H ),8.12 (d,J= 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.02 (d,J= 8.1H z,1H ),4.86-4.85 (m,1H ),3.25 (q,J= 7.5Hz,2H),1.97-1.72 (m,4H),1.70-1.61 (m,1H ),1.60-1.45 (m,2H),1.37 (t,J= 7.5 Hz,3H),1.10-0.93 (m,1H ),0.87 (d,J= 6.3 Hz,1H ). HPLC purity (254 nm): 99.5%.j0402j 2-(Benzo jbjthiophen-3-yl)-8-ethyl-5-(((1R,3S)-3-methylcyclohexyl)oxy)quinoline-4-carboxylic acid (Compound 182): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (brs,1H ),9.26 (d,J= 7.5 Hz,1H ),8.81 (s,1H ),8.12 (d,J= 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.02 (d,J= 8.1H z,1H ),4.86-4.85 (m,1H ),3.25 (q,J= 7.5Hz,2H),1.97-1.72 (m,4H),1.70-1.61 (m,1H ),1.60-1.45 (m,2H),1.37 (t,J 7.5 Hz,3H),1.10-0.93 (m,1H ),0.87 (d,J= 6.3 Hz,1H ). HPLC purity (254 nm): 99.7%.j0403j 2-(Benzo jbjthiophen-3-yl)-8-ethyl-5-(((1S,3S)-3-methylcyclohexyl)oxy)quinoline-4-carboxylic acid (Compound 183): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (s,1H ),9.27 (d,J= 7.8 Hz,1H ),8.81 (s,1H ),8.12 (d,J 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.11 (d,J= 8.1H z,1H ),4.50-4.57 (m,1H ),3.24 (q,J= 7.5Hz,2H),2.10-2.13 (m,2H),1.47-1.80 (m,3H),1.29-1.43 (m,5H),1.10-1.28 (m,1H ),0.94 (d,J= 6.6 Hz,3H),0.79-0.89 (m,1H ). HPLC purity (254 nm): 99.6%.j0404j 2-(Benzo jbjthiophen-3-yl)-8-ethyl-5-(((1R,3R)-3-methylcyclohexyl)oxy)quinoline-4-carboxylic acid (Compound 184): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (s,1H ),9.27 (d,J= 7.8 Hz,1H ),8.81 (s,1H ),8.12 (d,J 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.11 (d,J= 8.1H z,1H ),4.50-4.57 (m,1H ),3.24 (q,J= 7.5Hz,2H),2.10-2.13 (m,2H),1.47-1.80 (m,3H),1.29-1.43 (m,5H),1.10-1.28 (m,1H ),0.94 (d,J= 6.6 Hz,3H),0.79-0.89 (m,1H ). HPLC purity (254 nm): 99.7%.
As the paragraph descriping shows that 5381-20-4 is playing an increasingly important role.
Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MUNOZ, Benito; BASTOS, Cecilia, M.; PARKS, Daniel; KOMBO, David; (301 pag.)WO2017/62581; (2017); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem