Month: October 2020

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 tetrazoloquinoline aldehyde 1a (1 mmol) and rhodanine 2a (1 mmol), 20 mol % [HDBU][HSO4] was added, and the mixture was heated on an oil bath at 80 C for 30 min. During the reaction process, the mixture was solidified and after completion of the reaction (monitored by TLC), the reaction was cooled to room temperature, water was added and stirred for 5 min. The solid obtained was removed by filtration and recrystallized from EtOH-DMF. The filtrate was dried under reduced pressure to recover ionic liquid and reused in subsequent cycles.

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

Reference£º
Article; Subhedar, Dnyaneshwar D.; Shaikh, Mubarak H.; Nawale, Laxman; Yeware, Amar; Sarkar, Dhiman; Khan, Firoz A. Kalam; Sangshetti, Jaiprakash N.; Shingate, Bapurao B.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2278 – 2283;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

As a common heterocyclic compound, it belongs to thiazolidine compound, name is 2-(4-((2,4-Dioxothiazolidin-5-yl)methyl)phenoxy)acetic acid, and cas is 179087-93-5, its synthesis route is as follows.,179087-93-5

(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…

With the complex challenges of chemical substances, we look forward to future research findings about 179087-93-5,belong thiazolidine compound

Reference£º
Patent; Daiichi Sankyo Company, Limited; EP1894929; (2008); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO441,mainly used in chemical industry, its synthesis route is as follows.,1438-16-0

General procedure: General procedure for synthesis of N-substituted-rhodanine derivatives RhAs: To a solution of aldehydes (3a-3h, 1.0 equiv.) in ethanol (10 mL) was added slowly to the solution of 3-amino-2-thioxothiazolidin-4-one (2, 1.0 equiv.) in EtOH. The reaction mixture was stirred at room temperature without a catalyst for between 4 h and 12 h, and was monitored by TLC. After, the mixture product was recrystallized from EtOH. After recrystallization, N-substituted-rhodanine derivatives (RhAs) were obtained as follows.

With the synthetic route has been constantly updated, we look forward to future research findings about 3-Aminorhodanine,belong thiazolidine compound

Reference£º
Article; Bayindir; Caglayan, Cuneyt; Karaman, Muhammet; Guelcin, ?lhami; Bioorganic Chemistry; vol. 90; (2019);,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

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 tetrazoloquinoline aldehyde 1a (1 mmol) and rhodanine 2a (1 mmol), 20 mol % [HDBU][HSO4] was added, and the mixture was heated on an oil bath at 80 C for 30 min. During the reaction process, the mixture was solidified and after completion of the reaction (monitored by TLC), the reaction was cooled to room temperature, water was added and stirred for 5 min. The solid obtained was removed by filtration and recrystallized from EtOH-DMF. The filtrate was dried under reduced pressure to recover ionic liquid and reused in subsequent cycles.

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

Reference£º
Article; Subhedar, Dnyaneshwar D.; Shaikh, Mubarak H.; Nawale, Laxman; Yeware, Amar; Sarkar, Dhiman; Khan, Firoz A. Kalam; Sangshetti, Jaiprakash N.; Shingate, Bapurao B.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2278 – 2283;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

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 the compound (58 mg) produced in Reference Example 7 in DMF (1 mL), cesium carbonate (51 mg) and 1,3-propanesultam (20 mg) were added, and the resulting mixture was stirred overnight at 50C. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by Biotage SNAP KP-NH (hexane : ethyl acetate). The resulting purified product was dissolved in dimethoxyethane (1 mL) and methanol (1 mL), then an aqueous solution of sodium hydroxide (2 mol/L, 130 muL) was added, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was neutralized with a hydrochloric acid aqueous solution, followed by concentration under reduced pressure. The resulting residue was washed with water in slurry, and washed with acetonitrile in slurry to obtain the compound (46 mg) of the present invention having the following physical property values. HPLC retention time (min): 2.90; MS (ESI, Pos.): 555.23 (M+H)+; 1H-NMR (CDCl3): delta 1.65-1.83, 2.24-2.61, 3.08, 3.13-3.25, 4.10-4.23, 5.78, 6.45, 7.03-7.13, 7.26, 7.51, 7.63, 8.19, 8.89, 9.41.

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

Reference£º
Patent; ONO Pharmaceutical Co., Ltd.; ASADA, Masaki; TANI, Kousuke; HIGUCHI, Satonori; EP3632898; (2020); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO273,mainly used in chemical industry, its synthesis route is as follows.,5908-62-3

Compound 20: N-(3-(9H-Carbazol-9-yl)-2-hydroxypropyl)isothiazolidine 1,1-dioxide To a stirred solution of 1,3-propanesultam (0.80 g, 6.6 mmol) in anhydrous N,N-dimethylformaide (20 mL) was added sodium hydride (60% in mineral oil, 0.053 g, 1.3 mmol) and the mixture was stirred at room temperature for 1 hour. 9-(Oxiran-2-ylmethyl)-9H-carbazole (1.622 g, 7.3 mmol) was added and the mixture was stirred at 70 C. overnight. After cooling, the reaction was diluted with water and extracted three times with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated. The residue was purified by silica gel column chromatography (0-70% ethyl acetate in hexanes) and then recrystallized from ethyl acetate/hexanes to give the pure compound as a white solid (1.6 g, 70%). 1H NMR (300 MHz, CDCl3) delta 8.10 (d, 2H, J=7.5 Hz), 7.48 (d, 4H, J=3.9 Hz), 7.30-7.22 (m, 2H), 4.55-4.35 (m, 3H), 3.42-3.12 (m, 6H), 2.59 (d, 1H, J=3.0 Hz), 2.37 (m, 2H). ESI (m/z): 344.9 (M+H). HPLC analysis: (C18, 10-90% acetonitrile in water+0.1% trifluoroacetic acid over 10 min: retention time, % area at 254 nm): 11.8 min, >98%.

With the synthetic route has been constantly updated, we look forward to future research findings about 1,1-Dioxo-isothiazolidine,belong thiazolidine compound

Reference£º
Patent; Bersot, Ross; Humphries, Paul; US2013/303524; (2013); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

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: 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.

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
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;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

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 7025-19-6,belong thiazolidine compound

Reference£º
Article; Xue, Fengtian; MacKerell Jr., Alexander D.; Heinzl, Geoffrey; Hom, Kellie; Tetrahedron Letters; vol. 54; 13; (2013); p. 1700 – 1703;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO184,mainly used in chemical industry, its synthesis route is as follows.,5908-62-3

A 40 mL scintillation vial was charged with 1 ,1-dloxo-isothiazolidine (115 mg, 0.949 mmol) and OMF (3 mL). The reaction mixture was cooled to 00C and sodium hydride (95 mg, 2.373 mmol) was added. The reaction was left to stir at room temperature for 20 min foliowed by the addition of 3-bromo~5-(chloromethyl)pyridine hydrochloride (277 mg, 1.139 mmol). The reaction was stirred at room temperature for 3 h, then quenched with water and extracted with ethyi acetate. The organic layer was washed with water twice, dried over sodium sulfate and concentrated in vacuo. The crude was purified by silica gei flash chromatography using heptane-ethyl acetate (6(MO, v/v) to afford 3-bromo-5-(1,1- dioxo-isothiazolidin-2?ylmethyl)?pyridine as a colorless oil. MS (ESI) m/z 292.9 <;M+H)+ With the complex challenges of chemical substances, we look forward to future research findings about 1,1-Dioxo-isothiazolidine,belong thiazolidine compound Reference£º
Patent; NOVARTIS AG; CHAMOIN, Sylvie; HU, Qi-Ying; PAPILLON, Julien; WO2010/130796; (2010); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

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

Example 6-1 (Z)-3-(5-(2,5-dimethoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoic acid 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).

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

Reference£º
Patent; Senomyx, Inc.; US2009/274632; (2009); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com