Heterocyclic Building Blocks-Thiazolidine

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

General procedure: O-phenylenediamines (0.065 mol) was heated with N-aminorhodanine (0.065 mol) in xylene (50 ml) for 5 hours. The obtained residue was filtered and was crystallized from aqueous alcohol (charcoal). The obtained solid was recrystallized in ethanol.

With the complex challenges of chemical substances, we look forward to future research findings about 1438-16-0,belong thiazolidine compound

Reference£º
Article; El Kihel; Ait Sir; Jebbari; Ahbala; Guesmi; Bauchat; Oriental Journal of Chemistry; vol. 32; 4; (2016); p. 1765 – 1768;,
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As a common heterocyclic compound, it belongs to thiazolidine compound, name is 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, and cas is 7025-19-6, its synthesis route is as follows.,7025-19-6

General procedure: The suspension of 2-thioxo-1,3-thiazolidin-4-one (0.01 mol) 1a-40a in ethanol (50 mL) was mixed under stirring with a solution of aldehyde (0.011 mol) 1b-40b followed by the addition 3 drops of piperidine under the reflux conditions. The resulting mixture was heated under reflux until complete disappearance of 2-thioxo-1,3-thiazolidin-4-one, TLC control CH3OH – EtOAc 1:9. The reaction mixture was diluted with water (75 mL) and filtrated. The solid residue was recrystallized from a mixture of IPA/DMF.

With the complex challenges of chemical substances, we look forward to future research findings about 7025-19-6,belong thiazolidine compound

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Article; Volynets, Galyna P.; Bdzhola, Volodymyr G.; Golub, Andriy G.; Synyugin, Anatoliy R.; Chekanov, Maksym A.; Kukharenko, Oleksandr P.; Yarmoluk, Sergiy M.; European Journal of Medicinal Chemistry; vol. 61; (2013); p. 104 – 115;,
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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

To a solution of 3-iodo-N-(3,4,5-trifluorophenyl)-4,5,6,7-tetrahydropyrazolo[l,5- a]pyridine-5-carboxamide (compound lh, 20 mg, 0.048 mmol) in DMSO (1.0 mL) was added Cul (2 mg, 0.0095 mmol), K2C03 (7 mg, 0.095 mmol), N,N’-dimethyl-l,2-cyclohexanediamine (2 mg, 0.0095 mmol), and 1,2-thiazolidine 1,1-dioxide (compound 5a, 5 mg, 0.057 mmol). The reaction mixture was stirred at 110 C for 18 hours and then purified by flash chromatography and prep-HPLC to give 3-(l,l-dioxo-l,2-thiazolidin-2-yl)-N-(3,4,5-trifluorophenyl)-4,5,6,7- tetrahydropyrazolo[l,5-a]pyridine-5-carboxamide (Example 5, 11.5 mg) as a white solid. 1H NMR (400MHz, CDC13) delta 8.21 (s, 1H), 7.56 (s, 1H), 7.41 – 7.26 (m, 2H), 4.27 – 4.14 (m, 1H), 4.07 (m, 1H), 3.73 – 3.54 (m, 2H), 3.36 (t, 2H), 3.25 – 3.08 (m, 2H), 2.84 – 2.72 (m, 1H), 2.60 – 2.39 (m, 3H), 2.34 – 2.21 (m, 1H). MS obsd. (ESI+) [(M+H)+]: 415

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HU, Taishan; SHEN, Hong; HAN, Xingchun; (45 pag.)WO2018/11100; (2018); A1;,
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It is a common heterocyclic compound, the thiazolidine compound, (S)-4-Benzylthiazolidine-2-thione, cas is 171877-39-7 its synthesis route is as follows.,171877-39-7

A solution cooled in an ice bath of (S)-4-benzylthiazolidin-2-thione (18.37g, 87.87mmol) in CH2Cl2 (266mL) was treated with Et3N (2 eq) and then with 4-phenylbutanoyl chloride (Intermediate XI.1, 114.23mmol). The resulting mixture was stirred at room temperature for 12 days and then quenched with brine and extracted with CH2Cl2, dried with Na2SO4, filtered and concentrated. Purification by silica gel chromatography using Hex:AcOEt mixtures of increasing polarity (95:5, 9:1, 8:2, 7:3 and 6:4) afforded 24g (70%) of a yellow oil. 13C-NMR (500MHz, CDCl3) delta 201.06, 173.73, 141.53, 136.56, 129.44, 128.88, 128.53, 128.36, 127.19, 125.96, 68.53, 37.93, 36.79, 35.11, 31.90, 26.43.

With the complex challenges of chemical substances, we look forward to future research findings about (S)-4-Benzylthiazolidine-2-thione

Reference£º
Patent; Universitat Jaume I; EP2168954; (2010); A1;,
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1,1-Dioxo-isothiazolidine, cas is 5908-62-3, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.,5908-62-3

Example 98 Preparation of Intermediate 100 [0785] [0786] To an oven dried 50 mL round-bottom flask, methyl 2-bromo-5-methylbenzoate (352 mg, 1.54 mmol), sultam (236 mg, 1.95 mmol), cesium carbonate (732 mg, 2.25 mmol), palladium acetate (40.4 mg, 0.18 mmol), and Xanphos (136 mg, 0.235 mmol) were added and flask was placed under argon. The reagents were suspended in 8 mL of anhydrous dioxane and mixture was heated at 100 C. overnight. After cooling to room temperature, the reaction mixture was filtered, washing with ethyl acetate. The combined filtrate was concentrated under reduced pressure and resulting film was purified by silica gel column chromatography (25-100% ethyl Acetate in hexanes) to yield intermediate 100 (322 mg, 78%) as a yellow off-white solid. [0787] 1H-NMR (DMSO, 400 MHz): delta 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). [0788] LCMS m/z [M+H]+ C12H15NO4S requires: 270.07. Found 270.12.

5908-62-3 is used more and more widely, we look forward to future research findings about 1,1-Dioxo-isothiazolidine

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Patent; Siegel, Dustin; Sperandio, David; Yang, Hai; Sangi, Michael; Parrish, Jay P.; Hui, Hon Chung; US2013/273037; (2013); A1;,
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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

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+).

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

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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
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As a common heterocyclic compound, it belongs to thiazolidine compound, name is 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, and cas is 7025-19-6, its synthesis route is as follows.,7025-19-6

3-(4-oxo-2-thioxothiazolidin-3-yl)propanoic acid (200 mg, 1 mmol), 2,5-dimethoxy benzaldehyde (168 mg, 1 mmol) and piperidine (0.3 mL) were combined in ethanol (3 mL) and irradiated in the microwave at 100 C. for 10 minutes. The reaction was cooled, the solid was collected by filtration, washed with ethyl acetate/hexanes (1/1) and recrystallized from ethanol to afford 85% yield of the title compound (309 mg, brown-orange solid). MS (M+H, 284); 1H NMR (400 MHz, DMSO-d6): delta, ppm: 2.57 (t, 2H)), 3.74 (s, J=6.8 Hz, 3H), 3.84 (s, 3H), 4.19 (t, 2H), 6.90 (s, 1H), 7.10 (s, 2H), 7.86 (s, 1H). The compound had an IC50 on hT2R14 bitter receptor of 2.75 muM.

7025-19-6 is used more and more widely, we look forward to future research findings about 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid

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Patent; Senomyx, Inc.; Karanewsky, Donald S.; Fotsing, Joseph R.; Tachdjian, Catherine; Arellano, Melissa; (240 pag.)US9247759; (2016); B2;,
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3-Aminorhodanine, cas is 1438-16-0, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.,1438-16-0

General procedure: A mixture of aminorhodanine (1 mmol), isatin (1 mmol) and 5 muL of acetic acid in 2mL of distilled ethanol was placed in a cylindrical quartz reactor (Phi = 4 cm). The reactor was introducedinto a monomode microwave (Anton Paar) apparatus, for 5 min at100 C and 50 Watts. The crude reaction mixture was allowed tocool down at room temperature and ethanol (10 mL) or mixture of H2O/EtOH (10 mL) was directly added in the cylindrical quartzreactor. The resulting precipitated product was filtered off and waspurified by recrystallization from ethanol if necessary.

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

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Article; Khaldoun, Khadidja; Safer, Abdelmounaim; Boukabcha, Nourdine; Dege, Necmi; Ruchaud, Sandrine; Souab, Mohamed; Bach, Stephane; Chouaih, Abdelkader; Saidi-Besbes, Salima; Journal of Molecular Structure; vol. 1192; (2019); p. 82 – 90;,
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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

1,2-thiazolidine 1,1-dioxide (0.031 g, 0.259 mmol) in dimethylformamide (1 mL) was treated with 60% sodium hydride (0.012 g, 0.518 mmol, 0.021 g of a 60% in oil dispersion). The reaction mixture was stirred for 5 min. To this solution was added Example 41b (0.05 g, 0.086 mmol). The reaction mixture was stirred at room temperature for 2 hours. 2 N NaOH (1 mL) was added and the reaction mixture was heated at 65 C. for 2 hours. After cooling to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by preparative HPLC (C18, 10-80% acetonitrile in 0.1% TFA water) to afford 0.025 g (64%) of the title compound. 1H NMR (500 MHz, DMSO-d6) delta 2.21-2.25 (m, 2H), 3.15 (t, J=6.97 Hz, 2H), 3.23-3.27 (m, 2H), 3.50 (s, 3H), 4.13 (s, 2H), 6.25-6.26 (m, 1H), 6.88 (d, J=7.63 Hz, 2H), 7.00 (d, J=8.54 Hz, 1H), 7.03-7.05 (m, 1H), 7.25-7.30 (m, 4H), 7.34 (dd, J=8.39, 2.29, 1H), 7.48 (d, J=2.44 Hz, 1H), 12.00 (s, 1H). MS (ESI+) m/z 450.2 (M+H)+.

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

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Patent; WANG, Le; PRATT, John K; McDANIEL, Keith F.; DAI, Yujia; FIDANZE, Steven D; HASVOLD, Lisa; Holms, John H.; KATI, Warren M.; LIU, Dachun; Mantei, Robert A; McCLELLAN, William J.; SHEPPARD, George S.; Wada, Carol K.; US2014/162971; (2014); A1;,
Thiazolidine – Wikipedia
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As a common heterocyclic compound, it belongs to thiazolidine compound, name is 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, and cas is 7025-19-6, its synthesis route is as follows.,7025-19-6

General procedure: To a mixture of 5-chloroisatin (182 mg, 1.0 mmol) and N-carboxyethylrhodanine (205 mg, 1.0 mmol) was added DMSO-d6 (3.0 mL). The reaction was followed by proton NMR until the disappearance of the starting material.

With the complex challenges of chemical substances, we look forward to future research findings about 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid

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Article; Xue, Fengtian; MacKerell Jr., Alexander D.; Heinzl, Geoffrey; Hom, Kellie; Tetrahedron Letters; vol. 54; 13; (2013); p. 1700 – 1703;,
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