Category: thiazolidine

2-Cyanoimino-1,3-thiazolidine, cas is 26364-65-8, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

Add 0.01 mol to a 250 mL three-necked flask5-chloromethyl-3-(2,6-difluorophenyl)-1,2,4-oxadiazole,0.01mol2-(cyanoimino)thiazolidine,80mL DMF, stirring reaction at 80 C for 4h, TLC detection reaction is completed,Add distilled water, suction filtration, and dryness.Obtained 2.57g of a white solid.The yield was 80%., 26364-65-8

As the rapid development of chemical substances, we look forward to future research findings about 26364-65-8

Reference£º
Patent; Qingdao University of Science and Technology; Xu Liangzhong; Sun Jianxin; Cui Huanqi; Wang Minghui; (8 pag.)CN109320471; (2019); A;,
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7025-19-6,3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, cas is 7025-19-6, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

General procedure: To a mixture of aldehyde (1.0 mmol), 3-(4-oxo-2-thioxothiazolidin-3-yl)propanoic acid (205 mg,1.0 mmol) or 3-(2-(1H-tetrazol-5-yl)ethyl)-2-thioxothiazolidin-4-one (229 mg, 1.0 mmol) and NaOAc (820 mg, 10.0 mmol) was added acetic acid (5.0 mL). The reaction was allowed to stir at 105 C for 0.5h – 12h, then cooled to room temperature. To the reaction was added water (15mL). The resulting mixture was sonicated to give yellow-orange slurry. After filtration, the solid was washed with water (75 mL) and dried under high vacuum to yield the corresponding product as a red fine powder.

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Reference£º
Article; Liang, Dongdong; Robinson, Elizabeth; Hom, Kellie; Yu, Wenbo; Nguyen, Nam; Li, Yue; Zong, Qianshou; Wilks, Angela; Xue, Fengtian; Bioorganic and Medicinal Chemistry Letters; vol. 28; 6; (2018); p. 1024 – 1029;,
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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.

To a stirred solution of KHMDS in THF (1 M, 0.410 ml_, 0.410 mmol) and THF (1 mL) at 0 C was added a solution of 1 , 1-dioxo-isothiazolidine (0.044 g, 0.35 mmol) in THF (0.5ml_). The reaction mixture was stirred for 30 minutes at 0 C and then 3-[4-(bromomethyl)-3-chloro-phenyl]-5- (trifluoromethyl)-1 ,2,4-oxadiazole (0.100 g, 0.293 mmol), prepared according to procedures described in example 1 using 3-chloro-4-methyl-benzonitrile as starting material, was added. The reaction mixture was stirred at 0C for 2 h. The reaction mixture was then quenched with water and warmed to RT. The mixture was extracted with ethyl acetate and the combined organic layers washed with brine, dried over MgSC , filtered and concentrated under reduce pressure. LC/MS (Method A) retention time = 1.07 minutes, 398 (M+OH)”. The mass observed only in the negative ionization and corresponded to that of a hydrated species.

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Reference£º
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; POULIOT, Martin; BEAUDEGNIES, Renaud; (96 pag.)WO2017/93348; (2017); A1;,
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3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, cas is 7025-19-6, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.,7025-19-6

General procedure: A mixture of the selected aldehyde (0.75 mmol), 3-(2?- hydroxycarbonylethyl)-2-thioxothiazolidin-4-one (0.75 mmol, 159 mg) and anhydrous sodium acetate (2.25 mmol, 187 mg) in glacial acetic acid (0.75 mL) was thoroughly mixed in an appropriate 10 mL thick-walled glass vial. This was tightly sealed with a Teflon cap and the reaction mixture was stirred and heated at 140 C for 5 minutes, under focused microwave irradiation, with an initial power setting of 75 W. After cooling to room temperature, the yellow solid that precipitated from the crude product mixture was washed with distilled water, filtered under reduced pressure, recrystallized from dichloromethane and dried at room temperature under vacuum, yielding the desired compound as a bright-yellow solid. See, e.g., Figure 1. Yield: 83%, 215 mg; mp (C): 216-217; FT-JR (v, cm?): 3512, 3012, 1691, 1585, 1520, 1441, 1429, 1386,1314, 1253, 1218, 1171, 1152, 1106, 1075, 1025, 1005, 993, 937, 916, 873, 845, 792,734, 710, 622, 597, 566, 557, 536, 500; UV-vis (CH3OH): Xfflax, nm (relative absorbance, = 283 (70.3), 388 (100), 453 (17.2); ?H NMR (400 MHz, (CD3)2SO/CCL): oe, ppm =7.67 (1H, s, CH), 7.19 (2H, d, J= 7.6 Hz, ArH), 4.27 (2H, t, J= 7.8 Hz,NCH2CH2CO2H), 2.61 (2H, t, J= 7.8 Hz, NCH2CH2CO2H); ?3C NMR (100 MHz,(CD3)2SO/CCL): oe,ppm= 191.9, 171.1, 166.3, 152.3 (dd,J= 243.3 and 7.6 Hz), 137.1(t, J= 16.1 Hz), 131.4, 122.9 (t, J= 8.6 Hz), 120.9, 113.9 (dd, J= 15.2 and 7.4 Hz), 39.7,30.6; HR-MS (EJ): mlz = 344.9946 (M, C,3H9F2N0452 required 344.9941).

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

Reference£º
Patent; BSIM2 ? BIOMOLECULAR SIMULATIONS LDA; PONTES MEIRELES FERREIRA DE BRITO, Rui Manuel; VIEIRA SIMOES, Carlos Jose; DE VASCONCELOS DIAS DE PINHO MELO, Teresa Margarida; DA SILVA VICTOR, Bruno Lourenco; LOURENCO DE ALMEIDA, Zaida Catarina; CABRAL LOPES, Ana Lucia; OLIVEIRA NASCIMENTO, Bruno Filipe; (182 pag.)WO2016/80853; (2016); A1;,
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3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, cas is 7025-19-6, it is a common heterocyclic compound, the thiazolidine compound, 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 rapid development 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; 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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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.,5908-62-3

Example 26: (lR.25.7R.85f)-5-r7-(l.l-Dioxo-llambda6-isothiazolidin-2 -yl)-l.1- dioxo-l,4-dihydro-llambda6-benzori,2,41thiadiazin-3-yll-3-(4-fluoro-benzyl)-6-hydroxy-3- aza-tricvclor6.2.1.02’7lundec-5-en-4-one[00353] A reaction flask was charged with copper (I) iodide (8 mg, 0.042 mmol), sarcosine (N-methyl glycine) (9 mg, 0.1 mmol), isothiazolidine 1,1 -dioxide (204 mg, 1.685 mmol), (lR,25′,7R,85r)-3-(4-fluoro-benzyl)-6-hydroxy-5-(7-iodo-l,l- dioxo-l,4-dihydro-llambda6-benzo[l,2,4]thiadiazin-3-yl)-3-aza-tricyclo[6.2.1.02’7]undec-5- en-4-one (prepared as described in Example 19, 100 mg, 0.168 mmol) and potassium phosphate (179 mg, 0.842 mmol). The flask was degassed and backfilled with nitrogen, and then anhydrous NN-dimethylformamide (3 mL) was added. The resulting suspension was vigorously stirred at 100 0C for 17 h, and then allowed to cool to 25 0C. The mixture was diluted with ethyl acetate (30 mL) and washed with 1.0 M aqueous hydrochloric acid solution (2 x 20 mL) and saturated aqueous brine solution (40 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by flash column chromatography (Teledyne Isco RediSep column; 1st column: 100% dichloromethane, 2n column: 5% hexanes in dichloromethane) to afford the desired product. The crude product was triturated with absolute ethanol (3 x) and dried in vacuo at 60 0C to afford the desired product, ( R,2S,1R, 8S>5 -[7-(1,I -dioxo- 1 lambda6-isothiazolidin-2-yl)- 1 , 1 -dioxo- 1 ,4-dihydro- 1 lambda6- benzo[l,2,4]thiadiazin-3-yl]-3-(4-fluoro-benzyl)-6-hydroxy-3-aza- tricyclo[6.2.1.02’7]undec-5-en-4-one (70 mg, 0.119 mmol, 71%), as a solid. 1H nuMR (400 MHz, DMSO-de) delta: 1.17 – 1.24 (2H, m), 1.40 – 1.61 (4H, m), 2.39 – 2.46 (2H, m), 2.51 – 2.54 (IH, m), 2.64 – 2.65 (IH, m), 3.03 – 3.05 (IH, m), 3.53 – 3.60 (3H, m), 3.83 (2H, t, J= 6.3 Hz), 4.43 (IH, d, J= 15.4 Hz), 4.97 (IH, d, J= 15.6 Hz), 7.15 (2H, t, J= 9.0 Hz), 7.32 – 7.35 (2H, m), 7.51 – 7.54 (2H, m), 7.62 (IH, d, J= 8.5 Hz). LC-MS (ESI) calcd for C27H27FN4O6S2 586.14, found 587.4 [M+H+].

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

Reference£º
Patent; ANADYS PHARMACEUTICALS, INC.; WO2008/124450; (2008); A1;,
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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.,5908-62-3

Into a 4 mL vial was added isothiazolidine 1,1-dioxide (9.04 mg, 0.075 mmol) and (S)-6-chloro-3-(1-(4-chloropyrimidin-2-ylamino)ethyl)quinolin-2(1H)-one IV-1 (25 mg, 0.075 mmol) in DMF (250 muL). To this solution was added Cs2CO3 (48.6 mg, 0.149 mmol) and DIEA (26.1 muL, 0.149 mmol) and the reaction mixture was stirred at 110 C. for 1.5 hours. The mixture was then diluted with EtOAc and washed with brine (*2). The organic extract was dried over Na2SO4, filtered, and concentrated under reduced pressure to provide the crude product. This crude material was purified by column chromatography on a Biotage chromatography system (eluted with 0-100% EtOAc in hexanes) to afford the title compound (5.2 mg, 17% yield). 1H NMR (300 MHz, CDCl3): delta ppm 8.03 (br s, 1H), 7.93 (br s, 1H), 7.61 (br s, 1H), 7.41 (br d, J=8.50 Hz, 2H), 6.70 (br s, 1H), 5.42 (br s, 1H), 4.03 (br s, 1H), 3.83 (br s, 1H), 3.46 (m, 2H), 3.38 (m, 2H), 1.55-1.71 (m, 3H). LCMS (Method 1): Rt 2.02 min, m/z 419.89[M+H]+.

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

Reference£º
Patent; Forma Therapeutics, Inc.; Lin, Jian; Ericsson, Anna; Campbell, Ann-Marie; Gustafson, Gary; Wang, Zhongguo; Diebold, R Bruce; Ashwell, Susan; Lancia, JR., David R.; Caravella, Justin Andrew; Lu, Wei; (171 pag.)US2016/83365; (2016); A1;,
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179087-93-5, 2-(4-((2,4-Dioxothiazolidin-5-yl)methyl)phenoxy)acetic acid is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(Example 3) tert-Butyl N-{2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetylamino}-5-methoxyphenyl}-N-methylcarbamate Acetonitrile (400 ml) was added to 4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetic acid (40.0 g, 142.2 mmol). After cooling to an internal temperature of 7C, thionyl chloride (18.4 g, 155.0 mmol) was added. Dimethylformamide (32 ml) was further added and the mixture was stirred at the same temperature to 11.4C for three hours. A solution of tert-butyl N-(2-amino-5-methoxyphenyl)-N-methylcarbamate (38.4 g, 137.9 mmol) and triethylamine (18.7 g, 184.9 mmol) in acetonitrile (240 ml) maintained at 0 to 10C was added dropwise thereto over 65 minutes while cooling to maintain the reaction temperature at 0 to 5C, and then the mixture was further stirred at the same temperature for two hours. Next, water (320 ml) was added over 15 minutes and the mixture was stirred at an internal temperature of 0 to 5C for 2.5 hours. Thereafter, the precipitated crystals were separated by filtration. The resulting crystals were washed with a 2:1 solution of acetonitrile and water (160 ml) and dried under reduced pressure at 50C for 19 hours to obtain crystals of tert-butyl N-{2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetylamino}-5-methoxyphenyl}-N-methylcarbamate (63.6 g, 123.4 mmol) (yield: 89%).(Example 4) tert-Butyl N-{2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetylamino}-5-methoxyphenyl}-N-methylcarbamate (4-1) (The same lots of 4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetic acid and tert-butyl N-(2-amino-5-methoxyphenyl)-N-methylcarbamate as used in Example 3 were used in this example, respectively). Acetonitrile (400 ml) was added to 4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetic acid (40.0 g, 142.2 mmol). After cooling to an internal temperature of 8C, thionyl chloride (18.4 g, 155.0 mmol) was added. Dimethylformamide (32 ml) was further added and the mixture was stirred at the same temperature to 12C for three hours. A solution of tert-butyl N-(2-amino-5-methoxyphenyl)-N-methylcarbamate (38.4 g, 137.9 mmol) and triethylamine (18.7 g, 184.9 mmol) in acetonitrile (240 ml) maintained at 0 to 10C was added dropwise thereto over 65 minutes while cooling to maintain the reaction temperature at 0 to 3C, and then the mixture was further stirred at the same temperature for 3.5 hours. Next, water (320 ml) was added over 27 minutes and the mixture was stirred at 0 to 5C for 2.5 hours. Thereafter, the precipitated crystals were separated by filtration. The resulting crystals were washed with a 2:1 solution of acetonitrile and water (160 ml) and then dried under reduced pressure at 50C for 15 hours to obtain crystals of tert-butyl N-{2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetylamino}-5-methoxyphenyl}-N-methylcarbamate (67.6 g, 131.0 mmol) (yield: 92%).(4-2) A suspension of the crystals of tert-butyl N-{2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetylamino}-5-methoxyphenyl}-N-methylcarbamate obtained in (4-1) (56.1 g, 108.6 mmol) in methanol (1680 ml) was heated with stirring (the crystals were completely dissolved when the internal temperature reached 65.5C). The reaction solution was cooled to 0 to 5C over two hours and further stirred at the same temperature for 95 minutes, and then the precipitated crystals were separated by filtration. The resulting crystals were washed with methanol (224 ml) and then dried under reduced pressure at 50C for 15 hours to obtain purified crystals of tert-butyl N-{2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetylamino}-5-methoxyphenyl}-N-methylcarbamate (51.6 g, 100.0 mmol) (yield: 92%, total yield: 85%).(Example 6) {5-4-[(6-Methoxy-1-methyl-1H-benzimidazol-2-yl)methoxy]benzyl}thiazolidine-2,4-dione hydrochloride (6-1) Acetonitrile (140.9 kg) was added to 4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetic acid (18.0 kg, 64.0 mol). After cooling to an internal temperature of 8C, thionyl chloride (8.3 kg, 69.8 mol) was added. Dimethylformamide (14.4 L) was further added and the mixture was stirred at the same temperature to 15C for 3.5 hours. A solution of tert-butyl N-(2-amino-5-methoxyphenyl)-N-methylcarbamate (15.7 kg, 62.2 mol) and triethylamine (8.4 kg, 83.0 mol) in acetonitrile (84.6 kg) maintained at 0 to 10C was added dropwise thereto over one hour while cooling to maintain the reaction temperature at 0 to 5C, and then the mixture was further stirred at the same temperature for two hours. Next, water (144 L) was added over 22 minutes, and the mixture was stirred for 30 minutes while maintaining the internal temperature at 0 to 6C and then allowed to stand for 12 hours. The resulting crystals were separated by filtration and then washed with a 2:1 solution of water (54 L) to obtain wet crystals of tert-butyl N-{2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetylamino}-5-methoxyphenyl}-N-methylcarbamate.(6-2) A suspension of the wet crystals of tert-butyl N-{2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetylamino}-5-methoxyphenyl}-N-m…

179087-93-5, The synthetic route of 179087-93-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Daiichi Sankyo Company, Limited; EP1894929; (2008); A1;,
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A common heterocyclic compound, the thiazolidine compound, name is 1,1-Dioxo-isothiazolidine,cas is 5908-62-3, mainly used in chemical industry, its synthesis route is as follows.

5908-62-3, Step 2-1-(1,1-dioxo-isothiazolidin-2-ylmethyl)-3-benzyl-5-bromo-benzene (8B) A mixture of 8A (5 g, 14.7 mmol), 1,3-propanesultam (3.6 g, 29.7 mmol) and potassium carbonate (4.1 g, 29.7 mmol) in acetonitrile (60 mL) was refluxed overnight. The solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and brine. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatograph (ethyl acetate/hexanes) to give 8B as a white solid.

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Patent; Zhuang, Linghang; Wai, John S.; Payne, Linda S.; Young, Steven D.; Fisher, Thorsten E.; Embrey, Mark W.; Guare, James P..; US2005/10048; (2005); A1;,
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A common heterocyclic compound, the thiazolidine compound, name is 3-Aminorhodanine,cas is 1438-16-0, mainly used in chemical industry, its synthesis route is as follows.

General procedure: Two indole groups, 1H-indole-3-carbaldehyde (1) and 5-Bromo-1H-indole-3-carbaldehyde (2) (Sigma-Aldrich) were used as the primary core for insertion of the substituents 3-amino-2-thioxo-thiazolidin-4-one, 2-thioxo-thiazolidin-4-one, thiazolidin-2,4-dione and 2-thioxo-imidazolidin-4-one. The substituents were obtained commercially, except thiazolidin-2,4-dione that was synthesized in our laboratory according to the methodology of Brown [69].Prior to this reaction process, the groups 3a, 3b, 3c and 3d were solubilized in ethanol in the presence of morpholine and left stirring for 10 minutes at a temperature of 65 C. After this, indole nucleus (1 and 2) was added to the reaction system to obtain the final derivatives. Change of color was observed in all reactions after addition of indoles and precipitate formation 20min later. The reaction was monitored by thin layer chromatography (TLC) to check product formation and termination of the reaction. In general, the reaction lasted about 1h. As the reaction finished, the products were filtered and subjected to purification by successive washing with ethanol. The purity of the products was verified by 1H NMR, 13C NMR, mass spectroscopy and infrared.

1438-16-0, As the rapid development of chemical substances, we look forward to future research findings about 1438-16-0

Reference£º
Article; Lafayette, Elizabeth Almeida; de Almeida, Sinara Monica Vitalino; Cavalcanti Santos, Renata Virginia; de Oliveira, Jamerson Ferreira; Amorim, Cezar Augusto da Cruz; da Silva, Rosali Maria Ferreira; Pitta, Maira Galdino da Rocha; Pitta, Ivan da Rocha; de Moura, Ricardo Olimpio; de Carvalho Junior, Luiz Bezerra; de Melo Rego, Moacyr Jesus Barreto; de Lima, Maria do Carmo Alves; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 511 – 522;,
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