5908-62-3, Rate laws may be derived directly from the chemical equations for elementary reactions. This is not the case, however, for ordinary chemical reactions.5908-62-3, name is 1,1-Dioxo-isothiazolidine, below Introduce a new synthetic route.
5908-62-3, To a stirred solution of racemic 3-fluoro-2-({9-fluoro-6-methanesulfonyl-3-[4- (2H3)methyl-l-methyl-lH-l,2,3-triazol-5-yl]-5H-pyrido[3,2-b]indol-5-yl}(oxan-4- yl)methyl)pyridine (80.0 mg, 0.140 mmol) and isothiazolidine- 1,1 -dione (69.8 mg, 0.580 mmol) in NMP (0.70 mL) was added t-BuOK (56.5 mg, 0.500 mmol). The mixture was heated at 65 C for 70 min and cooled to room temperature. The mixture was diluted with water and extracted with EtOAc. Combined EtOAc extracts were dried (MgSCn), filtered, and concentrated. The crude product was purified by silica gel column chromatography (Teledyne ISCO CombiFlash 0% to 100% solvent A/B= DCM/10% MeOH/DCM, RediSep Si02 12 g, detecting at 254 nM, and monitoring at 220 nM). Concentration of appropriate fractions provided racemic 2-{5-[(3-fluoropyridin-2- yl)(oxan-4-yl)methyl]-6-methanesulfonyl-3-[4-(2H3)methyl-l-methyl-lH-l,2,3-triazol-5- yl]-5H-pyrido[3,2-b]indol-9-yl}-l 6,2-thiazolidine-l,l-dione (110 mg). This racemic mixture was separated by chiral prep SFC (Berger SFC MGII, ColummChiral IB 25 X 2.1 cm ID, 5muiotaeta Flow rate: 50.0 mL/min. Mobile Phase: 80/20 CC /MeOH Detector Wavelength: 220 nm) to give Enantiomers A (13.3 mg, 13%) and B (10.5 mg, 11%). Enantiomer A: NMR (400MHz, CDCb) delta 8.57 (d, J=1.8 Hz, 1H), 8.46 (dt, J=4.4, 1.5 Hz, 1H), 8.40 (d, J=8.6 Hz, 1H), 8.15 (d, J=2.0 Hz, 1H), 7.77 (d, J=8.6 Hz, 1H), 7.41- 7.28 (m, 3H), 4.34-4.24 (m, 1H), 4.21-4.11 (m, 1H), 4.01 (br dd, J=12.0, 2.7 Hz, 1H), 3.95 (s, 3H), 3.82 (br dd, J=11.6, 3.1 Hz, 1H), 3.61-3.53 (m, 2H), 3.46 (br d, J=2.3 Hz, 1H), 3.43 (s, 3H), 3.34 (br d, J=11.7 Hz, 1H), 3.20 (td, J=l 1.9, 1.9 Hz, 1H), 2.84-2.71 (m, 2H), 1.89-1.74 (m, 3H), 0.54 (br d, J=13.0 Hz, 1H); SFC RT = 10.07 min (Column: Chiralcel IB 250 x 4.6 mm, 5 muiotaeta; Mobile Phase: 80/20 CCh/MeOH; Flow: 2 mL/min); Enantiomer B: NMR (400MHz, CDCb) delta 8.56 (d, J=1.8 Hz, 1H), 8.45 (dt, J=4.3, 1.4 Hz, 1H), 8.40 (d, J=8.6 Hz, 1H), 8.15 (d, J=1.8 Hz, 1H), 7.76 (d, J=8.6 Hz, 1H), 7.42- 7.28 (m, 3H), 4.34-4.24 (m, 1H), 4.22-4.12 (m, 1H), 4.01 (br dd, J=11.7, 2.8 Hz, 1H), 3.95 (s, 3H), 3.82 (br dd, J=l 1.3, 3.2 Hz, 1H), 3.56 (dt, J=7.7, 3.9 Hz, 2H), 3.46 (br d, J=2.4 Hz, 1H), 3.43 (s, 3H), 3.37-3.28 (m, 1H), 3.23-3.15 (m, 1H), 2.84-2.69 (m, 2H), 1.79 (br dd, J=12.8, 4.2 Hz, 3H), 0.54 (br d, J=12.8 Hz, 1H) LCMS (M+H) = 556.2; SFC RT = 12.21 min (Column: Chiralcel IB 250 x 4.6 mm, 5 muiotaeta; Mobile Phase: 80/20 CCh/MeOH; Flow: 2 mL/min).
This molecular description is the mechanism of the reaction; it describes how individual atoms, ions, or molecules interact to form particular products.If you are interested, you can also browse other articles of 1,1-Dioxo-isothiazolidine, We look forward to the emergence of more reaction modes in the future.
Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; HAN, Wen-Ching; DEGNAN, Andrew P.; DESKUS, Jeffrey A.; GAVAI, Ashvinikumar V.; GILL, Patrice; SCHMITZ, William D.; STARRETT, John E., Jr.; (193 pag.)WO2016/183115; (2016); A1;,
Thiazolidine – Wikipedia
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