Category: 5908-62-3

5908-62-3, 1,1-Dioxo-isothiazolidine is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 5-{9-fluoro-6-methanesulfonyl-5-[(S)-oxan-4- yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-3-yl}-4-(2H3)methyl-l-methyl-lH-l,2,3- triazole (40.0 mg, 0.075 mmol) and isothiazolidine 1,1-dioxide (36.1 mg, 0.298 mmol) in NMP (0.40 mL) was added t-BuOK (29.2 mg, 0.261 mmol). This mixture was heated at 65 C for 2 h and cooled to room temperature. The mixture was purified via preparative LC/MS with the following conditions: Column: Waters XBridge Phenyl, 19 x 200 mm, 5- muiotaeta particles; Mobile Phase A: 5:95 ACN: water with 10 mM NH4OAC; Mobile Phase B: 95:5 ACN: water with 10 mM NH4OAC; Gradient: 15-70% B over 20 min, then a 5-min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give 9.6 mg. (20%). NMR (500MHz, DMSO-de) delta 8.72 (s, IH), 8.38 (d, J=8.4 Hz, IH), 7.89 (s, IH), 7.62 (br d, J=8.1 Hz, 3H), 7.37 – 7.30 (m, 2H), 7.26 (s, IH), 6.82 (br d, J=10.4 Hz, IH), 4.11 (br s, 2H), 3.86 (br d, J=8.4 Hz, IH), 3.77 (s, 3H), 3.75 (s, 3H), 3.65 (br d, J=8.8 Hz, IH), 3.57 (br t, J=7.4 Hz, IH), 3.53 – 3.45 (m, IH), 3.40 (br d, J=12.1 Hz, IH), 3.19 (br t, J=11.6 Hz, IH), 2.62 (quin, J=7.1 Hz, 2H), 2.52 – 2.52 (m, IH), 1.95 (br d, J=12.5 Hz, IH), 1.77 – 1.58 (m, 2H), 0.43 (br d, J=12.5 Hz, IH); LCMS: RT = 1.573 min; (ES): m/z (M+H)+ = 638.05; LCMS: Column: Waters Acquity UPLC BEH CI 8, 2.1 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 5:95 ACN:water with 10 mM LtOAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH40Ac;Temperature: 50 C; Gradient: 0-100% B over 3 min, then a 0.75 min hold at 100% B; Flow: 1.11 mL/min. HPLC Purity 220nm: 99 %.

5908-62-3 1,1-Dioxo-isothiazolidine 642157, athiazolidine compound, is more and more widely used in various.

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
Thiazolidine – ScienceDirect.com

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5908-62-3,1,1-Dioxo-isothiazolidine,as a common compound, the synthetic route is as follows.

To a stirred solution of 5-{9-fluoro-6-methanesulfonyl-5-[(S)-oxan-4- y l(pheny l)methy 1] -5H-py rido [3,2-b] indol-3 -y 1 } – 1 ,4-dimethy 1- 1H- 1 ,2,3-triazole (25.0 mg 0.0500 mmol) and isothiazolidine-l,l-dione (5.7 mg, 0.0500 mmol) in DMF (0.25 mL) was added t-BuOK (21.0 mg, 0.190 mmol). This mixture was heated at 65 C for 1.5 h and cooled to room temperature. The mixture was then diluted with MeOH and purified via preparative LC/MS with the following conditions: Column: Waters XBridge Phenyl, 19 x 200 mm, 5-mutaueta particles; Mobile Phase A: 5:95 ACN: water with 10 mM NH4OAC; Mobile Phase B: 95:5 ACN: water with 10 mM NH4OAc; Gradient: 15-70% B over 20 min, then a 5-min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give 2-[3-(dimethyl-lH- l,2,3-triazol-5-yl)-6-methanesulfonyl-5-[(S)-oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2- b]indol-9-yl]- 6,2-thiazolidine-l,l-dione (12.3 mg, 41%). NMR (500MHz, DMSO- de) delta 8.72 (s, IH), 8.38 (d, J=8.4 Hz, IH), 7.88 (s, IH), 7.62 (br d, J=8.4 Hz, 3H), 7.36- 7.30 (m, 2H), 7.27 (br d, J=7.1 Hz, IH), 6.81 (br d, J=10.1 Hz, IH), 4.11 (br d, J=2.0 Hz, 2H), 3.86 (br d, J=9.8 Hz, IH), 3.76 (s, 3H), 3.74 (s, 2H), 3.64 (br d, J=8.8 Hz, IH), 3.57 (br t, J=7.4 Hz, IH), 3.19 (br t, J=12.1 Hz, IH), 2.65-2.57 (m, 2H), 2.54 (s, 3H), 2.07 (s, 3H), 1.95 (br d, J=12.5 Hz, IH), 1.75-1.56 (m, 2H), 0.42 (br d, J=12.1 Hz, IH). LCMS: RT = 1.414 min; (ES): m/z (M+H)+ = 634.95; LCMS: Column: Waters Acquity UPLC BEH C18, 2.1 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 5:95 ACN:water with 10 mM NH4OAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH4OAC; Temperature: 50 C; Gradient: 0-100% B over 3 min, then a 0.75-min hold at 100% B; Flow: 1.11 mL/min. HPLC Purity at 220 nm: 100 %

The synthetic route of 5908-62-3 has been constantly updated, and we look forward to future research findings.

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
Thiazolidine – ScienceDirect.com

5908-62-3, 1,1-Dioxo-isothiazolidine is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 5-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[l,2,3]triazolo[4,5-d] pyrimidine (15.9 mg, 47.2 muiotaetaomicron?), 1,1-dioxo-isothiazolidine (11.4 mg, 94.4 muiotaetaomicron?) and DBU (14.2 mu?^, 94.4 mumol) in DMF (250 mu?) was stirred at the room temperature overnight. The reaction mixture was directly purified by preparative HPLC (column: Gemini 5um C18 110A 75 x 30mm. mobile phase: water (0.05% Et3N): acetonitrile 75:25% to 5:95%. WL: 230 nm Flow: 30 mL/min.) to afford the title compound as white solid (3.10 mg, 16%). MS(m/e): 387.3 (MH+).

The synthetic route of 5908-62-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; ADAM, Jean-Michel; BISSANTZ, Caterina; GRETHER, Uwe; KIMBARA, Atsushi; NETTEKOVEN, Matthias; ROEVER, Stephan; ROGERS-EVANS, Mark; WO2013/68306; (2013); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5908-62-3,1,1-Dioxo-isothiazolidine,as a common compound, the synthetic route is as follows.

To an oven dried 50 mE round-bottom flask, methyl2-bromo-5-methylbeioate (352 mg, 1.54 mmol), sultam(236 mg, 1.95 mmol), cesium carbonate (732 mg, 2.25mmol), palladium acetate (40.4 mg, 0.18 mmol), and Xanphos (136 mg, 0.23 5 mmol) were added and flask was placedunder argon. Reagents were suspended in 8 mE of anhydrousdioxane and mixture was heated at 100 C. overnight. Aftercooling to room temperature, reaction mixture was filtered,was1ng with ethyl acetate. Combined filtrate was concen446.04trated under reduced pressure and resulting film was purifiedby silica gel column chromatography (25-100% EthylAcetate in Hexanes) to yield intermediate 11.?H-NMR (DMSO, 400 MHz): oe 7.75 (d, 1H), 7.44 (m, 1H),7.35 (m, 1H), 3.89 (s, 3H), 3.81 (t, 2H), 3.28 (t, 2H), 2.55 (m,2H), 2.39 (s, 3H).ECMS m/z [M+H] C12H15N04S requires: 270.07. Found270.12.

As the paragraph descriping shows that 5908-62-3 is playing an increasingly important role.

Reference£º
Patent; Gilead Sciences, Inc.; Sangi, Michael; (125 pag.)US9278975; (2016); B2;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

5908-62-3, 1,1-Dioxo-isothiazolidine is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 26.1.3: Preparation of 3-Benzyloxy-7-(l,l-dioxo-isothiazolidin-2-yl)-4- oxo-4H-pyrido[l,2-fl]pyrimidine-2-carboxylic acid 4-fluoro-benzylamide; The product from Example 26.1.2 (100 mg, 0.189 mmol), isothiazolidine 1,1-dioxide (46 mg, 0.378 mmol), copper(I) iodide (4 mg, 0.019 mmol), N,N-dimethylethyl diamine (3 mg, 0.039 mmol) and potassium carbonate (55 mg, 0.378 mmol) were mixed in DMF (4.0 mL) and heated to 80 0C. After 2 h, TLC indicated that the reaction was complete. The reaction mixture was cooled to room temperature and poured into aqueous hydrochloric acid (1.0 M, 40 mL. The resulting solid was collected by filtration and washed with water, dried and subjected to column chromatography (dichloromethane/methanol 50:1) to afford the desired product (93 mg, 95%).1H NMR (300 MHz, D6-DMSO) delta 3.64 (2H, t, J=I. ,3 Hz, cyclic-(SO2)-CH2CH2CH2N), 3.89 (2H, t, J=6.5 Hz, cyclic-(SO2)-CH2CH2CH2N-), 4.43 (2H, d, J=5.9 Hz, NHCH2), 5.14 (2H, s, CH2O)D7.06 (2H, t, J=9.0 Hz, ArH), 7.32-7.48 (7H, m, ArH), 7.84 (IH, d, J=9.9 Hz, ArH), 8.00 (IH, dd, J=2.8, 9.7 Hz, ArH), 8.61 (IH, d, J=2.6 Hz, ArH), 9.07 (IH, t, J=6.2 Hz 5 NHCH2).

5908-62-3 1,1-Dioxo-isothiazolidine 642157, athiazolidine compound, is more and more widely used in various.

Reference£º
Patent; AVEXA LIMITED; WO2008/77188; (2008); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5908-62-3,1,1-Dioxo-isothiazolidine,as a common compound, the synthetic route is as follows.

3-CYCLOBUTYL-7- [ (5-IODO-2-PYRIDINYL) OXY]-2, 3,4, 5-TETRAHYDRO-1H-3-BENZAZEPINE (E207) (200 mg, 0.48 MMOL), isothiazolidine 1,1-dioxide (116 mg, 0.96 MMOL), (Evans, Brian J.; Takahashi Doi, Joyce; Musker, W. Kenndh J. Org. Chem.; 55; 9; 1990; 2580-2586) potassium carbonate (238 mg, 1.73 MMOL), copper (I) iodide (27 mg, 0.14 MMOL) and N, N- dimethylethylenediamine (0.02 ml, 0.14 MMOL) were added together in dry dioxane (3 ml) and heated in a microwave reactor at 140 C for 20 minutes. The mixture was diluted with methanol and applied to a SCX column eluting with methanol and then a mixture of. 880 AMMONIA/METHANOL (1: 9). The basic fractions were combined and concentrated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of. 880 ammonia: methanol : dichloromethane (0.5 : 4.5 : 95) to afford the title compound (145 mg); MS (ES+) M/E 414 [M+H] +.

5908-62-3 1,1-Dioxo-isothiazolidine 642157, athiazolidine compound, is more and more widely used in various.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2004/56369; (2004); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5908-62-3,1,1-Dioxo-isothiazolidine,as a common compound, the synthetic route is as follows.

To a mixture of Intermediate 1 (1 equiv.) and isothiazo lidine 1,1-dioxide (1.2 equiv.) in 1 ,4-dioxane was added cesium carbonate (1.5 equiv.). The reaction was heated to 100 C for 16 h, after which the reaction was diluted with water, and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified via silica gel chromatography utilizing a 3-10% methanol in dichloromethane gradient to deliver the desired compound, Compound 1-503 (71.3 mg, 73% yield) as an off- white solid.1H-NMR (500 MHz, CDC13) oe 8.57 (d, 1 H), 8.47 (d, 1 H), 7.36 (s, 1 H), 7.20-7.25 (m, 1 H),7.03-7.07 (m, 1 H), 6.96-7.01 (m, 1 H), 6.84-6.88 (m, 1 H), 6.61 (m, 1 H), 5.99 (s, 2 H), 4.27 (t, 2 H), 3.44 (t, 2 H), 2.66 (t, 2 H).

The synthetic route of 5908-62-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NAKAI, Takashi; MOORE, Joel; PERL, Nicholas Robert; IYENGAR, Rajesh R.; MERMERIAN, Ara; IM, G-Yoon Jamie; LEE, Thomas Wai-Ho; HUDSON, Colleen; RENNIE, Glen Robert; JIA, James; RENHOWE, Paul Allen; BARDEN, Timothy Claude; YU, Xiang Y; SHEPPECK, James Edward; IYER, Karthik; JUNG, Joon; WO2014/144100; (2014); A2;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

5908-62-3, 1,1-Dioxo-isothiazolidine is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To 2-choro-5-nitro-3-trifluoromethypyridine (056 g, 2.48 mmo) and isothiazoHdine 1,1- dioxide (060 g, 496 mmo) in 1,4-dioxane (12 m) were added Cs2003 (0.81 g, 2.48 mmo) and argon was bubbed though the mixture for 10 mm. Then Xantphos (287 mg, 0,50 mrnoD and Pd2(dba)3 (114 mg, 0.124 mmoD were added. The reaction mixture was stirred for 40 mm at 140C in a microwave oven. The mixture was fi?tered through a pad of C&ite and the sovent was evaporated. The crude product was purified by flash co?umn chromatography on sihca ge (cyciohexane/AcOEt 100/0 to 50/50) to afford 2-(5- nitro-3-(trifluoromethy)pyridmn-2-y)isothiazoidine 1,1-dioxide. M/z = 312 [M+H]+, Rt = 0.87 mm (U PLC Method 32).

The synthetic route of 5908-62-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; PISSOT SOLDERMANN, Carole; QUANCARD, Jean; SCHLAPBACH, Achim; SIMIC, Oliver; TINTELNOT-BLOMLEY, Marina; ZOLLER, Thomas; (161 pag.)WO2015/181747; (2015); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

5908-62-3, 1,1-Dioxo-isothiazolidine is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 5 (0.109 g, 0.114 mmol) was combined with isothiazolidine 1,1-dioxide (0.139 g, 1.145 mmol) in anhydrous acetonitrile (1.1 mE). para-Toluenesulfonic acid monohydrate (0.0022 g, 0.011 mmol) was added. The reaction was stirred at room temperature for two hours. 10503] The reaction was diluted with saturated aqueous NaHCO3. The mixture was extracted several times with EtOAc. The organic extracts were combined, dried over Na2SO, decanted and concentrated to give a yellow tar crude product.10504] The crude product was purified by silica gel flash column chromatography (0-40% acetone-heptane, gradient elution, 24 g silica column, TEC in 40% acetone-heptane, visualize under UV) to give Example 17 (0.053 g, 0.046 mmol, 40.0% yield) as a white solid.Example 1710505] ESIMS [M+H] 1041.8, [M-H] 1039.8.10506] HRMS: calculated for C54H84N6012SNa-1063.5765. Found-1063.5759.10507] ?H NMR (600 MHz, Chloroform-d) oe 8.86 (s, 1H),6.39 (dd, J=14.7, 11.0 Hz, 1H), 6.22 (dd, J=14.7, 10.7 Hz,1H), 6.11 (dd, J=15.0, 10.5 Hz, 1H), 5.99 (d, J=10.9 Hz, 1H),5.34 (dd, J=14.9, 9.8 Hz, 1H), 5.18 (d, J=5.7 Hz, 1H), 5.10(d, J=9.8 Hz, 1H), 4.87 (m, 1H), 4.67 (m, 1H), 4.63 (d,J=12.2 Hz, 1H), 4.50 (s, 1H), 4.13 (d, J=6.1 Hz, 1H), 3.97(t, J=11.4 Hz, 1H), 3.78 (d, J=6.2 Hz, 1H), 3.69-3.62 (m,1H), 3.55 (dt, J=11.2, 4.0 Hz, 1H), 3.50-3.39 (m, 1H), 3.39(s, 3H), 3.38-3.30 (m, 1H), 3.27 (s, 3H), 3.25-3.13 (m, 1H),3.07 (td, J=8.4, 3.8 Hz, 1H), 3.01 (m, 1H), 2.96 (q, J=7.9 Hz,1H), 2.70-2.63 (m, 2H), 2.39 (m, 1H), 2.35-2.21 (m, 3H),2.18 (d, J=13.7 Hz, 1H), 2.16-2.09 (m, 1H), 1.95-1.81 (m,3H), 1.82 (s, 3H), 1.75 (m, 3H), 1.65 (s, 3H), 1.60 (m, 6H),1.58-1.50 (m, 1H), 1.53-1.34 (m, 2H), 1.32 (m, 1H), 1.29(m, 1H), 1.25 (m, 6H), 1.12 (m, 1H), 1.05 (d, J=6.6 Hz, 3H),1.05-0.78 (m, 12H).

The synthetic route of 5908-62-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; BONAZZI, Simone; CONNOLLY, Michael; GLASS, David Jonathan; MIHALIC, Manuel; PATTERSON, Andrew William; ROGGO, Silvio; SHAVLAKADZE, Tea; (68 pag.)US2019/92788; (2019); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5908-62-3,1,1-Dioxo-isothiazolidine,as a common compound, the synthetic route is as follows.

Under a nitrogen atmosphere, a solution of 5-bromo-6-chloro-pyridine-2-carboxylic acid methyl ester (Example 9 c, 1 g, 4 mmol), isothiazolidine 1,1-dioxide (730 mg, 06 mmol), copper(I) iodide (150 mg, 0.8 mmol), 1,3-di(pyridin-2-yl)propane-1,3-dione (CAN 10198-89-7, 180 mg, 0.8 mmol) and potassium carbonate (1.1 g, 8 mmol) in DMF (20 mL) was reacted for 24 h at 110 C. The reaction mixture was poured into water, and extracted with ethyl acetate (3¡Á50 mL). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography (silica gel, 4 g, 10% ethyl acetate in petroleum ether) to yield the title compound (0.048 g, 1.6 mmol, 41.4%) as yellow solid; MS (EI): m/e=291.0 [M+H]+.

5908-62-3 1,1-Dioxo-isothiazolidine 642157, athiazolidine compound, is more and more widely used in various.

Reference£º
Patent; Bissantz, Caterina; Grether, Uwe; Hebeisen, Paul; Kimbara, Atsushi; Liu, Qingping; Nettekoven, Matthias; Prunotto, Marco; Roever, Stephan; Rogers-Evans, Mark; Schulz-Gasch, Tanja; Ullmer, Christoph; Wang, Zhiwei; Yang, Wulun; US2012/316147; (2012); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com