With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61563-43-7,Isoquinoline-8-carboxylic acid,as a common compound, the synthetic route is as follows.
General procedure: To a suspension of the acid(0.25 mmol, 1.00 equiv) and N,N,N0 ,N0-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU) (0.25 mmol,1.00 equiv) in CH2Cl2 (2.5 mL), under an air atmosphere, at ambienttemperature, was added diisopropylethylamine (0.1 mL,0.58 mmol, 2.34 equiv) and the mixture was stirred for 25 min.2-((5-(Trifluoromethyl)pyridin-2-yl)sulfonyl)ethan-1-aminiumchloride(14) (0.26 mmol, 1.05 equiv) and CH2Cl2 (5 mL) were thenadded and the mixture was stirred for 48 h. The reaction wasquenched with aqueous HCl (1 M, 2 mL), followed by H2O(10 mL) and EtOAc (20 mL). The mixture was transferred to a separatoryfunnel and the flask rinsed with EtOAc (10 mL). The organicphase was separated, washed with saturated aqueous NaHCO3(15 mL) and dried over anhydrous Na2SO4. The solvent was thenremoved under reduced pressure, at or below 40 C, to afford thecrude product. Purification was performed as indicated for eachcompound below 5.3.6.12 N-(2-((5-(Trifluoromethyl)pyridin-2-yl)sulfonyl)ethyl)isoquinoline-8-carboxamide (42) The title compound was prepared from isoquinoline-8-carboxylic acid (0.043 g, 0.25 mmol). The crude product was purified by flash chromatography on silica gel (0:100-60:40/EtOAc:Heptane) affording a colourless solid (0.032 g, 0.08 mmol, 31%). 1H NMR (600 MHz, DMSO-d6) delta 9.58 (s, 1H), 9.18-9.15 (m, 1H), 8.71 (t, J = 5.4 Hz, 1H), 8.56 (dd, J = 8.2, 2.3 Hz, 1H), 8.54 (d, J = 5.7 Hz, 1H), 8.32 (d, J = 8.1 Hz, 1H), 8.05 (d, J = 8.2 Hz, 1H), 7.86 (d, J = 5.6 Hz, 1H), 7.76 (dd, J = 8.3, 7.1 Hz, 1H), 7.62 (dd, J = 7.2, 1.1 Hz, 1H), 3.93 (t, J = 6.5 Hz, 2H), 3.79 (q, J = 6.3 Hz, 2H). 13C NMR (151 MHz, DMSO-d6) delta 167.0, 159.9 (br s), 150.0, 147.0 (q, J = 3.9 Hz), 142.7, 136.8 (q, J = 3.6 Hz), 135.2, 133.7, 129.1, 128.6, 128.3 (q, J = 33.1, 32.7 Hz), 126.4, 124.6, 122.5 (q, J = 273.3 Hz), 122.1, 120.2, 50.5, 33.3 (q, J = 32.8 Hz). HRMS (ESI) Calcd for C18H14F3N3NaO3S [M+Na]+: 432.0600; found 432.0598 (0.5 ppm). HPLC (CH3OH:H2O/50:50, 1 mL/min, 254 nm) tr(minor) 4.41 min (<1%), tr(minor) 4.54 min (<1%), tr(minor) 8.00 min (<1%), tr(major) 9.23 min (99%).
The synthetic route of 61563-43-7 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Kaupang, Asmund; Kase, Eili Tranheim; Vo, Cecilie Xuan Trang; Amundsen, Marthe; Vik, Anders; Hansen, Trond Vidar; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 247 – 260;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem