Tag: M.W:100-200

As a common heterocyclic compound, it belongs to thiazolidine compound, name is 1,1-Dioxo-isothiazolidine, and cas is 5908-62-3, its synthesis route is as follows.,5908-62-3

To a stirred solution of 5-{9-fluoro-5-[(S)-(4-fluorophenyl)(oxan-4-yl)methyl]-6- methanesulfonyl-5H-pyrido[3,2-b]indol-3-yl}-4-(2H3)methyl-l-methyl-lH-l,2,3-triazole (24.0 mg, 0.0400 mmol) and isothiazolidine-l,l-dione (26.2 mg, 0.220 mmol) in NMP (0.25 mL) was added t-BuOK (19.4 mg, 0.170 mmol). This mixture was heated at 65 C for 2 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-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 2-{5-[(S)-(4- fluorophenyl)(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 (11.6 mg, 40%). NMR (500MHz, DMSO-de) delta 8.73 (s, IH), 8.37 (d, J=8.5 Hz, IH), 7.90 (s, IH), 7.71-7.65 (m, 2H), 7.61 (d, J=8.4 Hz, IH), 7.16 (br t, J=8.7 Hz, 2H), 6.78 (br d, J=10.2 Hz, IH), 4.10 (br t, J=6.8 Hz, 2H), 3.88 (br d, J=10.7 Hz, IH), 3.83 (s, 3H), 3.64 (br d, J=8.7 Hz, IH), 3.57 (br t, J=7.5 Hz, IH), 3.47 (br s, 2H), 3.39 (br s, IH), 3.17 (br t, J=11.4 Hz, IH), 2.66-2.57 (m, 2H), 2.54 (s, 3H), 1.90 (br d, J=12.6 Hz, IH), 1.64 (br t, J=12.1 Hz, 2H), 0.42 (br d, J= 1.8 Hz, IH). LCMS: RT = 1.670 min; (ES): m/z (M+H)+ = 656.15. LCMS: Column: Waters Acquity UPLC BEH C18, 2.1 x 50 mm, 1.7-muetaiota 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: 98 %

With the complex challenges of chemical substances, we look forward to future research findings about 5908-62-3,belong thiazolidine compound

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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As a common heterocyclic compound, it belongs to thiazolidine compound, name is 1,1-Dioxo-isothiazolidine, and cas is 5908-62-3, its synthesis route is as follows.,5908-62-3

(1S,2S)-N1,N2-Dimethylcyclohexane-1,2-diamine (46.1 mg, 0.30 mmol) and copper iodide (56.3 mg, 0.30 mmol) were added to a mixture of 2,3-dichloro-5-nitropyridine (571 mg, 2.96 mmol), isothiazolidine 1,1-dioxide (430 mg, 3.55 mmol) and potassium carbonate (817.5 mg, 5.92 mmol) in dioxane (6 mL) under N2. The reaction mixture was stirred at 100 C. for 16 h. The mixture was filtered, and the filtrate was extracted with ethyl acetate. The organic extracts were dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The resultant crude product was purified by flash chromatography (petroleum ether/ethyl acetate=100:0 to petroleum ether/ethyl acetate=50:50) to afford compound 58a as a white solid (600 mg, 73%).

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Reference£º
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
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Name is (R)-2-Oxothiazolidine-4-carboxylic acid, as a common heterocyclic compound, it belongs to thiazolidine compound, and cas is 19771-63-2, its synthesis route is as follows.,19771-63-2

(2) To 1.47 g of the compound obtained in Reference Example 1-(1) were successively added an aqueous solution comprising 1.5 ml of water and an aqueous solution containing 0.6 g of sodium hydroxide and 4.4 ml of dimethylsulfoxide under ice-cooling. To the mixture was added 2.3 ml of benzyl chloride at room temperature, and the resulting mixture was stirred for 15 hours. The mixture was neutralized by dil. hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then, insoluble material was filtered off and the filtrate was concentrated to give 2.24 g of (4R)-2-oxo-3-benzylthiazolidin-4-carboxylic acid as colorless crystal. Melting point: 95-97C MS ¡¤APCI (m/z): 238 [(M+H)+] [alpha]D25: -102.2 (C=1.0, chloroform).

With the complex challenges of chemical substances, we look forward to future research findings about (R)-2-Oxothiazolidine-4-carboxylic acid

Reference£º
Patent; TANABE SEIYAKU CO., LTD.; EP1462444; (2004); A1;,
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As a common heterocyclic compound, it belongs to thiazolidine compound, name is 3-Aminorhodanine, and cas is 1438-16-0, its synthesis route is as follows.,1438-16-0

B. Preparation of 5-[[3-(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-amino-2-thioxo-4-thiazolidinone The benzaldehyde intermediate from Example 78A (20.0 g; 112.2 mmol), N-aminorhodanine (18.29 g; 123.4 mmol) and sodium acetate (36.8 g; 448.8 mmol) were suspended in 560 ml of acetic acid. The suspension was heated to reflux, stirred at that temperature for 7 hours (at which time a precipitate had formed) and then cooled to room temperature with stirring. The precipitate was recovered by filtration and then washed successively with a 1:1 ethyl acetate/diethyl ether solution then a diethyl ether wash. The recovered precipitate was dried under vacuum at 60 C for 2 hours to provide 14.5 g of the desired subtitled intermediate. m.p. >225 C.

With the complex challenges of chemical substances, we look forward to future research findings about 3-Aminorhodanine

Reference£º
Patent; The University of Colorado Foundation, Inc.; US5158966; (1992); A;,
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(S)-4-Phenylthiazolidine-2-thione, cas is 185137-29-5, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.,185137-29-5

General procedure: Under N2 atmosphere, NaH (120 mg, 60% dispersion in mineral oil, 3 mmol)was added to a solution of thiazolidine-2-thione 2 (2.5 mmol) in 5 mL of THF and the resulting solution was cooled to 78C by a dry-ice-acetone bath. Propionyl chloride(255 mg, 2.5 mmol, 480 muL) was then dropped in. After removal of the solvent in vacuo,the residue was purified by column chromatography with a mixture of petroleum ether(60-90C)/EtOAc (5:1, v/v) as eluent.

185137-29-5 is used more and more widely, we look forward to future research findings about (S)-4-Phenylthiazolidine-2-thione

Reference£º
Article; Chen, Ning; Du, Hongguang; Liu, Weidong; Wang, Shanshan; Li, Xinyao; Xu, Jiaxi; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 190; 1; (2015); p. 112 – 122;,
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Name is 3-Aminorhodanine, as a common heterocyclic compound, it belongs to thiazolidine compound, and cas is 1438-16-0, its synthesis route is as follows.,1438-16-0

B. Preparation of 5-[[3-(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-amino-2-thioxo-4-thiazolidinone The benzaldehyde intermediate from Example 77A (20.0 g; 112.2 mmol), N-aminorhodanine (18.29 g; 123.4 mmol) and sodium acetate (36.8 g; 448.8 mmol) were suspended in 560 ml of acetic acid. The suspension was heated to reflux, stirred at that temperature for 7 hours (at which time a precipitate had formed) and then cooled to room temperature with stirring. The precipitate was recovered by filtration and then washed successively with a 1:1 ethyl acetate/diethyl ether solution then a diethyl ether wash. The recovered precipitate was dried under vacuum at 60 C. for 2 hours to provide 14.5 g of the desired subtitled intermediate. m.p. >225 C.

With the complex challenges of chemical substances, we look forward to future research findings about 3-Aminorhodanine

Reference£º
Patent; Eli Lilly and Company; US5731336; (1998); A;,
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5908-62-3,1,1-Dioxo-isothiazolidine, cas is 5908-62-3, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

100 mg (0.231 mmol) of (¡À)-1-(4-bromophenyl)-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-3H-2,3-benzodiazepine-3-carboxamide (Example 49A), 33.6 mg (0.278 mmol) of 1,2-thiazolidine 1,1-dioxide (CAS [5908-62-3]), 64 mg (0.46 mmol) of potassium carbonate and 13 mg (0.023 mmol) of allylchloropalladium dimer (CAS [12012-95-2]) are charged in 3 ml of 2-methyltetrahydrofuran and the suspension is degassed with argon for 10 min. Then 39 mg (0.093 mmol) of di-tert-butyl(2?,4?,6?-triisopropylbiphenyl-2-yl)phosphane (CAS [564483-19-8]) are added, degassing with argon is carried out again, and the mixture is heated at 80 C. for 16 h. The crude mixture is filtered, and then the solvent is removed and the residue obtained is purified by preparative HPLC. This gave 32 mg (29% of theory) of the desired product as a solid.

As the rapid development of chemical substances, we look forward to future research findings about 5908-62-3

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SIEGEL, STEPHAN; BAURLE, STEFAN; CLEVE, ARWED; HAENDLER, BERNARD; FERNANDEZ-MONTALVAN, AMAURY ERNESTO; MONNING, URSULA; KRAUSE, SABINE; LEJEUNE, PASCALE; SCHMEES, NORBERT; BUSEMANN, MATTHIAS; HOLTON, SIMON; KUHNKE, JOACHIM; (434 pag.)JP2015/529192; (2015); A;,
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Name is 1,1-Dioxo-isothiazolidine, as a common heterocyclic compound, it belongs to thiazolidine compound, and cas is 5908-62-3, its synthesis route is as follows.,5908-62-3

A Schlenk tube was charged with 5-[5-({3-[(1 R,5S/1 S,5R)-1-(4-bromophenyl)-3- azabicyclo[3.1.0]hex-3-yl]propyl}thio)-4-methyl-4H-1 ,2,4-triazol-3-yl]-2-methylquinoline (cf. Example 2; 0.15 g), isothiazolidine 1 ,1 -dioxide (46 mg), tris(dibenzylideneacetone)- dipalladium(O) (6 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (10 mg), cesium carbonate (130 mg) and 1 ,4-dioxane (2 mL). The Schlenk tube was sealed with a teflon screwcap and the reaction mixture was stirred at 100 0C for 12 h. The reaction mixture was allowed to cool to room temperature, diluted with dichloromethane (10 mL), filtered EPO and concentrated in vacuo. The crude product was purified by flash chromatography (dichloromethane to 10% MeOH in dichloromethane) to give 50 mg of the free base of the title compound. To a solution of this material in dichloromethane (0.3 mL) was added HCI (0.087 mL, 1 M in Et2O), the solvent evaporated in vacuo and the material thus obtained triturated with Et2O to give 52 mg of the title compound as a white solid.NMR (1H, DMSO): delta 10.57 (bs,1 H), 8.27 (bd, 1 H), 8.19 (d, 1 H), 7.94 (t, 1 H), 7.82 (d, 1 H), 7.55 (d, 1 H)1 7.32 (d, 2H), 7.18 (d, 2H), 4.03 (dd, 1H), 3.72 (m, 3H), 3.60/3.20 (bm, 8H), 3.45 (s, 3H), 2.75 (s, 3H), 2.41 (m, 2H), 2.25 (m, 2H), 2.14 (m, 1 H), 1.66/1.10 (t/m, 2H). MS (ml z) 575 [MH]+.

With the complex challenges of chemical substances, we look forward to future research findings about 1,1-Dioxo-isothiazolidine

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/22980; (2007); A1;,
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As a common heterocyclic compound, it belongs to thiazolidine compound, name is (S)-4-Phenylthiazolidine-2-thione, and cas is 185137-29-5, its synthesis route is as follows.,185137-29-5

b. 4-(S)-Phenyl-2-thione-thiazolidine-3-carboxylic acid-4-nitro-phenyl ester To a suspension of NaH (26 mg, 1.04 mmol) in 10 mL of anhydrous THF under argon, a solution of 4(S)-Phenyl-thiazolidine-2-thione (170 mg, 0.87 mmol) in THF was added dropwise via an dropping funnel. The resulting suspension was stirred at room temperature for 30 min. This suspension was then added dropwise via cannula into another round bottom flask containing a solution of 4-nitrophenylchloroformate (217 mg, 1.04 mmol) in 20 mL of THF and cooled at -78 C. over a period of 15 min. The stirring was continued for 2 h after which the solvent was removed and the residue was purified by column chromatography on silica gel with 1:1 hexane/CH2 Cl2 then 3:7 hexane/CH2 Cl2 followed by CH2 Cl2 (Rf =0.50) to obtain (+)-4(S)-phenyl-2-thione-thiazolidine-3-carboxylic acid-4-nitro-phenyl ester as a pale yellow solid (200 mg, 64%).

With the complex challenges of chemical substances, we look forward to future research findings about 185137-29-5,belong thiazolidine compound

Reference£º
Patent; Synaptic Pharmaceutical Corporation; US6159990; (2000); A;,
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As a common heterocyclic compound, it belongs to thiazolidine compound, name is 1,1-Dioxo-isothiazolidine, and cas is 5908-62-3, its synthesis route is as follows.,5908-62-3

Intermediate 6 (0.090 g, 0.093 mmol) was combined with isothiazolidine 1,1-dioxide (0.112 g, 0.926 mmol) in anhydrous dichloromethane (0.93 mE). paraToluenesulfonic acid monohydrate (1.761 mg, 9.26 tmol) was added in one portion. The reaction was stirred at room temperature for 100 minutes.10510] The entire reaction mixture was purified by silica gel flash column chromatography (0-40% acetone-heptane, gradient elution, 24 g silica column, TEC in 40% acetoneheptane, visualize under UV) to give a mixture of Example 18 and residual unreacted isothiazolidine 1,1-dioxide.10511] The mixed material was again purified by silica gel flash column chromatography (0-50% acetonitrile-dichloromethane, gradient elution, 24 g column, TEC in 30% acetonitrile-dichloromethane, visualize under UV) to give Example 18 (0.02 1 g, 0.019 mmol, 20.4% yield) as a white solid.Example 1810512] ESIMS [M+NH4] 1078.9, [M-H] 1059.9.10513] HRMS: calculated for C57H92N2014SNa sodiumadduct-1083.6167. Found 1083.6151.10514] ?H NMR (600 MHz, Chloroform-d) oe 6.45 (dd,J=14.5, 11.0 Hz, 1H), 6.21 (dd, J=14.6, 10.7 Hz, 1H), 6.14(dd, J=14.8, 10.8 Hz, 1H), 5.98 (d, J=10.9 Hz, 1H), 5.35 (dd,J=14.8, 9.8 Hz, 1H), 5.20 (d, J=5.8 Hz, 1H), 5.09 (d, J=9.8Hz, 1H), 4.72 (d, J=12.1 Hz, 1H), 4.61 (m, 1H), 4.46 (s, 1H),4.10 (d, J=6.9 Hz, 1H), 3.96 (t, J=11.4 Hz, 1H), **373 (t,J=5.5 Hz, 2H), 3.68 (d, J=6.9 Hz, 1H), 3.59 (m, 4H), 3.53(m, 2H), 3.46 (s, 3H), 3.28 (s, 3H), 3.21 (m, 1H), 3.13 (m,1H), 3.07 (m, 2H), 3.05-2.99 (m, 1H), 2.97 (q, J=8.0 Hz,1H), 2.78 (dq, J=14.4, 7.1 Hz, 1H), 2.44-2.33 (m, 1H), 2.31(m, 2H), 2.27-2.19 (m, 1H), 2.19-2.12 (m, 2H), 2.07-1.94 (m, 2H), 1.88 (s, 3H), 1.83 (d, J=12.9 Hz, 1H), 1.74 (m, 3H),1.66 (m, 7H), 1.56-1.44 (m, 1H), 1.43 (m, 2H), 1.41-1.15(m, 12H), 1.04 (m, 7H), 0.91 (m, 8H), 0.84 (d, J=6.7 Hz,3H), 0.70 (q, J=12.0 Hz, 1H).

With the complex challenges of chemical substances, we look forward to future research findings about 5908-62-3,belong thiazolidine compound

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;,
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