Category: thiazolidine

The thiazolidine compound, cas is 171877-39-7 name is (S)-4-Benzylthiazolidine-2-thione, mainly used in chemical industry, its synthesis route is as follows.

To an ice-bath cold solution of 35 (S)-4-benzylthiazolidine-2-thione13 (18.37g, 87.87mmol) and 36 Et3N (26.66mL, 175.74mmol) in 37 CH2Cl2 (266mL) was added 38 4-phenylbutanoyl chloride (freshly prepared from 39 4-phenylbutyric acid (17.31g, 105.44mmol)). The resulting mixture was stirred at room temperature for 24h. Then brine was added and extracted with CH2Cl2 (3¡Á40mL), the organic layers were washed (brine), dried (Na2SO4) and concentrated. The yellow crude oil was purified through chromatography (silica-gel, hexanes/40 EtOAc (98:2) and (95:5)) to afford 24.76mg (77%); [alphaD25]=+157.80 (c=2.3, CHCl3). IR (NaCl) nu 3025, 2935, 2849, 1603, 1695, 1496, 1454, 1342, 1394, 1359, 1342, 1293, 1264, 1192, 1157, 1135, 1040, 893, 746, 701cm-1. 1H NMR (500MHz, CDCl3) delta 7.16-7.34 (10H, m), 5.33 (1H, ddd, J=4.0, 7.5 and 11.5Hz), 3.38 (1H, ddd, J=6.0, 9.0 and 17.0Hz), 3.33 (1H, dd, J=7.5 and 11.5Hz), 3.13-3.20 (2H, m), 3.01 (1H, dd, J=10.5 and 13.0Hz), 2.84 (1H, d, J=11.5Hz), 2.68 (2H, t, J=7.0Hz). 13C NMR (125MHz, 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, 26.43ppm.. HRMS m/z calcd. for C20H21ONS2Na [M+Na+]: 378.0962, found: 378.0970; m/z calcd. for C20H21ONS2K [M+K+]: 394.0702, found: 394.0724.

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Article; Royo, Santiago; Schirmeister, Tanja; Kaiser, Marcel; Jung, Sascha; Rodriguez, Santiago; Bautista, Jose Manuel; Gonzalez, Florenci V.; Bioorganic and Medicinal Chemistry; vol. 26; 16; (2018); p. 4624 – 4634;,
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The thiazolidine compound, cas is 1438-16-0 name is 3-Aminorhodanine, mainly used in chemical industry, its synthesis route is as follows.

EXAMPLE 37 3-[(1,3-Benzodithiol-2-ylidene)amino]-2-thioxo-4-thiazolidinone A solution of N-(1,3-benzodithiol-2-ylidene)-N-methylbenzaminium iodide (3.85g), N-aminorhodanine (1.48g) and anhydrous sodium carbonate (530 mg) in 100 ml of anhydrous dimethylformamide is heated at 120 C under a nitrogen atmosphere for 2 hours. The reaction mixture is then poured into 500 ml of ice/water and left stirring at 4 C for 2 hours. The resultant precipitate is collected by filtration and washed several times with cold water. The solid is air dried to yield 2.0g of crude product. This product is recrystallized from dimethylformamide to yield 1.9g of the title compound, melting point 295-300 C. Anal. Calc’d. for C10 H6 N2 OS4: C, 40.25; H, 2.03; N, 9.39; S, 42.98. Found: C, 40.27; H, 2.20; N, 9.30; S, 43.05.

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Patent; E. R. Squibb & Sons, Inc.; US4104467; (1978); A;,
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The thiazolidine compound, cas is 5908-62-3 name is 1,1-Dioxo-isothiazolidine, mainly used in chemical industry, its synthesis route is as follows.

5908-62-3, To a stirred solution of racemic 3-fluoro-2-({9-fluoro-6-methanesulfonyl-3-[4- (2H3)methyl-l-methyl-lH-l,2,3-triazol-5-yl]-5H-pyrido[3,2-b]indol-5-yl}(oxan-4- yl)methyl)pyridine (80.0 mg, 0.140 mmol) and isothiazolidine- 1,1 -dione (69.8 mg, 0.580 mmol) in NMP (0.70 mL) was added t-BuOK (56.5 mg, 0.500 mmol). The mixture was heated at 65 C for 70 min and cooled to room temperature. The mixture was diluted with water and extracted with EtOAc. Combined EtOAc extracts were dried (MgSCn), filtered, and concentrated. The crude product was purified by silica gel column chromatography (Teledyne ISCO CombiFlash 0% to 100% solvent A/B= DCM/10% MeOH/DCM, RediSep Si02 12 g, detecting at 254 nM, and monitoring at 220 nM). Concentration of appropriate fractions provided racemic 2-{5-[(3-fluoropyridin-2- yl)(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 (110 mg). This racemic mixture was separated by chiral prep SFC (Berger SFC MGII, ColummChiral IB 25 X 2.1 cm ID, 5muiotaeta Flow rate: 50.0 mL/min. Mobile Phase: 80/20 CC /MeOH Detector Wavelength: 220 nm) to give Enantiomers A (13.3 mg, 13%) and B (10.5 mg, 11%). Enantiomer A: NMR (400MHz, CDCb) delta 8.57 (d, J=1.8 Hz, 1H), 8.46 (dt, J=4.4, 1.5 Hz, 1H), 8.40 (d, J=8.6 Hz, 1H), 8.15 (d, J=2.0 Hz, 1H), 7.77 (d, J=8.6 Hz, 1H), 7.41- 7.28 (m, 3H), 4.34-4.24 (m, 1H), 4.21-4.11 (m, 1H), 4.01 (br dd, J=12.0, 2.7 Hz, 1H), 3.95 (s, 3H), 3.82 (br dd, J=11.6, 3.1 Hz, 1H), 3.61-3.53 (m, 2H), 3.46 (br d, J=2.3 Hz, 1H), 3.43 (s, 3H), 3.34 (br d, J=11.7 Hz, 1H), 3.20 (td, J=l 1.9, 1.9 Hz, 1H), 2.84-2.71 (m, 2H), 1.89-1.74 (m, 3H), 0.54 (br d, J=13.0 Hz, 1H); SFC RT = 10.07 min (Column: Chiralcel IB 250 x 4.6 mm, 5 muiotaeta; Mobile Phase: 80/20 CCh/MeOH; Flow: 2 mL/min); Enantiomer B: NMR (400MHz, CDCb) delta 8.56 (d, J=1.8 Hz, 1H), 8.45 (dt, J=4.3, 1.4 Hz, 1H), 8.40 (d, J=8.6 Hz, 1H), 8.15 (d, J=1.8 Hz, 1H), 7.76 (d, J=8.6 Hz, 1H), 7.42- 7.28 (m, 3H), 4.34-4.24 (m, 1H), 4.22-4.12 (m, 1H), 4.01 (br dd, J=11.7, 2.8 Hz, 1H), 3.95 (s, 3H), 3.82 (br dd, J=l 1.3, 3.2 Hz, 1H), 3.56 (dt, J=7.7, 3.9 Hz, 2H), 3.46 (br d, J=2.4 Hz, 1H), 3.43 (s, 3H), 3.37-3.28 (m, 1H), 3.23-3.15 (m, 1H), 2.84-2.69 (m, 2H), 1.79 (br dd, J=12.8, 4.2 Hz, 3H), 0.54 (br d, J=12.8 Hz, 1H) LCMS (M+H) = 556.2; SFC RT = 12.21 min (Column: Chiralcel IB 250 x 4.6 mm, 5 muiotaeta; Mobile Phase: 80/20 CCh/MeOH; Flow: 2 mL/min).

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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;,
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The thiazolidine compound, cas is 179087-93-5 name is 2-(4-((2,4-Dioxothiazolidin-5-yl)methyl)phenoxy)acetic acid, mainly used in chemical industry, its synthesis route is as follows.

Examples (Example 1) 4-[(2,4-Dioxothiazolidin-5-yl)methyl]phenoxyacetyl chloride Thionyl chloride (170 mg, 1.34 mmol) and then pyridine (1 drop) were added to a suspension of 4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetic acid (220 mg, 0.78 mmol) in dichloromethane (10 ml) at room temperature, and the mixture was refluxed for 3.5 hours. The resulting solution was concentrated under reduced pressure to obtain about 250 mg of the gummy target compound. Nuclear magnetic resonance spectrum (400 MHz, DMSO-d6) delta (ppm): 3.05 (1H, dd, J = 9.0 Hz, J = 14.1 Hz, CH2CH), 3.31 (1H, dd, J = 4.1 Hz, J = 14.1 Hz, CH2CH), 4.64 (2H, s, CH2O), 4.87 (1H, dd, J = 4.1 Hz, J = 9.0 Hz, CH2CH), 6.85 (2H, d, J = 8.6 Hz, aromatic), 7.16 (2H, J = 8.6 Hz, aromatic), 12.02 (1H, s, NH).

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Patent; Daiichi Sankyo Company, Limited; EP1894929; (2008); A1;,
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The thiazolidine compound, cas is 1438-16-0 name is 3-Aminorhodanine, mainly used in chemical industry, its synthesis route is as follows.

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.

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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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Thiazolidin-2-one, cas is 2682-49-7, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

(d) A mixture containing 3.09 g (0.03 mol) of 2-thiazolidinone, 11.2 g of potassium carbonate, 1.8 g of potassium hydrogen carbonate, 0.5 ml of water, 30 ml of methyl isobutyl ketone and 3.0 ml (0.033 mol) of benzyl bromide is refluxed for 7 hours. After cooling down, the reaction mixture is washed twice with 30 ml of water each, the organic phase is dried and evaporated. The yellow oily product (which solidifies on standing) may be purified by column chromatography (by using Kieselgel 60 of 230-400 mesh as sorbent and chloroform as eluent) to give 3.2 g (55.2%) of the title compound, m.p.: 50-51 C.

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Patent; Richter Gedeon Vegyeszeti Gyar Rt.; US4937252; (1990); A;,
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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 86; N- (3-Cyclobutyl-2, 3, 4,5-tetrahydro-1 H-3-benzazepin-7-yl)-4- (1, 1-dioxido-2- isothiazolidinyl) benzamide (E86); A mixture of N- (3-cyclobutyl-2, 3,4, 5-tetrahydro-1 H-3-benzazepin-7-yl)-4-iodobenzamide (E11) (150mg, 0.34 mmol), potassium carbonate (169 mg, 1.22 mmol), copper (1) iodide (19 mg, 0.1 mmol), N,N’-dimethyl-1, 2-ethanediamine (0.01 ml, 0.1 mmol) and isothiazolidine 1,1-dioxide (123 mg, 1.0 mmol) in dioxan (3 ml) was heated in a microwave reactor at 140 C for 20 minutes. The mixture was diluted with methanol and purified on an SCX ion exchange cartridge eluting with methanol and then a 2M methanolic ammonia solution. The basic fractions were concentrated in vacuo and the residue purified by column chromatography eluting with a mixture of 2M methanolic ammonia solution and dichloromethane (3-97) to afford the title compound (E86) MS (ES+), m/e 440 [M+H] +.

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Patent; GLAXO GROUP LIMITED; WO2005/58837; (2005); 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, General procedure: To the mixture of the precursor 10(2.26 g, 10.1 mmol, 1.5 equiv) and tert-butyl 1,2,5-thiadiazolidine-2-carboxylate 1,1-dioxide (1.50 g, 6.75 mmol, 1.0 equiv) in dry DMF(10 mL), was added Cs2CO3 (6.60 g, 20.25 mmol, 3.0 equiv). Themixture was stirred at room temperature overnight, and thenextracted with ethyl acetate. The organic phase was washed withsaturated NaHCO3 and brine, dried over anhydrous Na2SO4, filteredand concentrated. The resulting residue was purified via silica gelchromatography to give 11a as colorless oil (1.96 g, 79%).

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Article; Chen, Shulun; Guo, Wei; Liu, Xiaohua; Sun, Pu; Wang, Yi; Ding, Chunyong; Meng, Linghua; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 38 – 55;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7025-19-6,3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid,as a common compound, the synthetic 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.

As the paragraph descriping shows that 7025-19-6 is playing an increasingly important role.

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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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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.

General procedure: Thiazolidin-2-ylidene-cyanamide (0.317 g, 2.50 mmol) inacetonitrile (20 mL) was dropwise added to a stirred solutionof substituted benzyl bromide (2.5 mmol) and 14 mL NaOHaqueous solution (1 M). The mixture is stirred at room temperaturefor 8-10 h. The soild was collected by filtration,washed with n-hexane and dried in vacuo.

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Article; Jia, Ai-Quan; Ma, Sen; Wang, Jun-Ling; Zhang, Qian-Feng; Journal of Chemical Crystallography; (2020);,
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