Heterocyclic Building Blocks-Thiazolidine

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

A microwave vial was charged with (5-{7-chloro-6-fluoro-5-[(S)-oxan-4- yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-3-yl}-4-(2H3)methyl-l-methyl-lH-l,2,3- triazole (30 mg, 0.061 mmol), isothiazolidine 1,1-dioxide (11.1 mg, 0.091 mmol), tripotassium phosphate (18.1 mg, 0.085 mmol), Pd2(dba)3 (2.8 mg, 3.0 muiotatauiotaomicron), 2-di-tert- butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-l, -biphenyl (2.9 mg, 6.1 mumol), and dry tert-butanol (0.5 mL). The reaction was heated at 84C overnight. It was diluted with water and extracted with ethyl acetate. The organic layer was concentrated and purified by preparative HPLC (Column: XBridge CI 8, 19 x 200 mm, 5-muiotatauiota particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 15-55% B over 15 min, then a 5-min hold at 100% B; Flow: 20 mL/min) to give 2.1 mg (6%). NMR (500 MHz, DMSO) delta 8.61 (s, 1H), 8.11 (m, 1H), 7.96 (s, 1H), 7.64 (m, 2H), 7.45 (m, 1H), 7.35 (m, 2H), 7.28 (m, 1H), 5.91 (m, 1H), 3.9 (m, 5H), 3.77 (m, 1H), 3.52 (m, 3H), 3.29 (m, 1H), 2.55 9m, 2H), 1.78 (m, 1H), 1.35 (m, 2H), 1.1 (m, 1H); LCMS (M+H) = 578.35

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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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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: A solution of 0.002 mol of rhodanine in 5 mL of ethanol and 0.05 mL of 2-aminoethanol were added to a solution of 0.002 mol of aldehyde 1 in 5 mL of ethanol. The mixture was refluxed for 2-3 h and cooled. The precipitate was filtered off and recrystallized.

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Article; Sinenko; Slivchuk; Pil?o; Raenko; Brovarets; Russian Journal of General Chemistry; vol. 86; 7; (2016); p. 1597 – 1603; Zh. Obshch. Khim.; vol. 86; 7; (2016); p. 1119 – 1125,7;,
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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.

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., 1438-16-0

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Article; Bayindir; Caglayan, Cuneyt; Karaman, Muhammet; Guelcin, ?lhami; Bioorganic Chemistry; vol. 90; (2019);,
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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.

7 mg (0.03 mmol) of palladium(II) acetate and 18 mg (0.03 mmol) of Xantphos were stirred in 3.6 ml of dioxane under an argon atmosphere at 20 C. for 10 minutes. Then 150 mg (0.3 mmol) of the compound from Example 72A, 74 mg (0.06 mmol) of 1,3-propane sultam and 148 mg (0.46 mmol) of caesium carbonate were added and the mixture was stirred at 110 C. for 6 h. After cooling down to 23 C., the mixture was purified via preparative HPLC (eluent: acetonitrile/water gradient with 0.1% formic acid). This gave 95 mg (51% of theory) of the title compound. LC-MS (Method 1): Rt=1.15 min; m/z=579.2 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 1.156 (4.54), 1.174 (8.71), 1.192 (4.39), 1.987 (16.00), 2.297 (4.76), 2.314 (6.89), 2.331 (5.14), 3.577 (4.62), 3.590 (8.77), 3.606 (8.06), 3.634 (2.43), 4.020 (4.03), 4.037 (3.96), 4.815 (3.11), 4.827 (3.16), 4.845 (3.08), 4.859 (2.88), 7.325 (3.46), 7.334 (7.37), 7.356 (6.87), 7.380 (2.99), 7.399 (5.75), 7.420 (4.45), 7.526 (13.43), 7.546 (9.83), 7.555 (3.20), 7.811 (2.87), 7.826 (2.86), 8.595 (6.46), 8.617 (6.25), 8.754 (11.28), 10.157 (2.54), 10.171 (4.84).

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Patent; Bayer Pharma Aktiengesellschaft; TELLER, Henrik; STRAUB, Alexander; BRECHMANN, Markus; MUeLLER, Thomas; MEININGHAUS, Mark; NOWAK-REPPEL, Katrin; TINEL, Hanna; MUeNTER, Klaus; FLIEGNER, Daniela; MONDRITZKI, Thomas; BOULTADAKIS ARAPINIS, Melissa; MARQUARDT, Tobias; VAKALOPOULOS, Alexandros; REBSTOCK, Anne-Sophie; WITTWER, Matthias Beat; (342 pag.)US2018/297994; (2018); A1;,
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185137-29-5, (S)-4-Phenylthiazolidine-2-thione is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,185137-29-5

General procedure: To a mixture of N-crotonyl oxazolidinone 7 (100 mg, 0.43 mmol) and 4-phenyl-2-oxazolidine-2-thione 4 (77.1 mg, 0.43 mmol) in dichloromethane (5.0 mL) was added triethylamine (131.2 mg, 1.29 mmol) at room temperature. The resulting mixture was stirred and heated to reflux overnight. After cooling to room temperature, water (10 mL) was added and the reaction mixture was extracted with CH2Cl2 (3 x 7 mL) The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude Michael addition product. The crude residue was purified by silica gel flash column chromatography.

185137-29-5 (S)-4-Phenylthiazolidine-2-thione 11333042, athiazolidine compound, is more and more widely used in various fields.

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Article; Munive, Laura; Dzakuma, Sena A.; Olivo, Horacio F.; Tetrahedron Letters; vol. 54; 10; (2013); p. 1230 – 1232;,
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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

Intermediate 4 (0.146 g, 0.150 mmol) and isothiazolidine 1,1-dioxide (0.181 g, 1.496 mmol) were dissolved into anhydrous acetonitrile (1.5 mE). para-Toluenesulfonic acid monohydrate (2.84 mg, 0.015 mmol) was added in one portion. The reaction mixture was stirred at room temperature for two hours.10479] Aqueous saturated NaHCO3 was added. The mixture was extracted several times with ethyl acetate. The organic extracts were combined, dried over Na2SO, decanted and concentrated to give a colorless tar crude product.10480] The crude product was dissolved in MeOH (2.5 mE) and was purified in one injection via preparative-scale reverse phase chromatography (40-90% acetonitrile-water plus 0.1% TFA modifier on 100 g C18 ISCO column).10481] The first eluting peak fractions were pooled and reduced to about volume on a rotary evaporatot The remaining solution was made basic with saturated aqueous NaHCO4 and was extracted several times with EtOAc. The organic extracts were combined, dried over Na SO4, decanted and concentrated to give Example 14 (0.05 g, 0.044 mmol, 29.3% yield) as a white solid.Example 1410482] ESIMS [M+NH4] 1082.8, [M-H] 1063.7.10483] HRMS: calculated for C55H89N2O14PSNa as sodium adduct-1087.5670. Found-1087.5725.10484] ?H NMR (400 MHz, Chloroform-d) oe 6.45 (dd, J=14.4, 10.9 Hz, 1H), 6.22 (dd, J=14.5, 10.6 Hz, 1H), 6.13 (dd, J=14.6, 10.5 Hz, 1H), 5.8 (d, J=10.8 Hz, 1H), 515 (dd, i=14.7, 9.8 Hz, 1H), 5.23-5.17 (m, 1H), 5.10 (d, J=9.8 Hz, 1H), 4.67 (m, 2H), 4.47 (d, J=1.8 Hz, 1H), 4.18-4.04 (m, 2H), 4.03-3.91 (m, 1H), 3.72 (d, J=6.5 Hz, 1H), 3.68-3.48 (m, 2H), 3.38 (m, 4H), 3.28 (s, 3H), 3.26-3.12 (m, 2H), .12-2.91 (m, 4H), 2.74 (m, HI), 2.48-2.26 (m, 3F1), 2.26- 2.12 (m, 3H), 2.12-2.04 (m, 2H), 1.87 (s, 3H), 1.85-1.72 (m, 4H), 1.72-1.54 (m, 12H), 1.54-1.43 (m, 6H), 1.43-1.33 (m, 3H), 1.33-1.21 (m, 2H), 1.21-1.09 (m, 2H), 1.03 (m, 7H),1.00-0.78 (m, 9H), 0.72 (q, J=11.9 Hz, 1H).10485] The second eluting peak fractions were pooled and reduced to about volume on the rotary evaporatot The remaining solution was made basic with saturated aqueous NaHCO3. The mixture was extracted several times with ethyl acetate. The organic extracts were combined, dried over Na2504, decanted and concentrated to give Example 15 (0.010 g, 7.51 tmol, 5.02% yield) as a white solid.Example 1510486] ESIMS [M+NH4] 1082.8 [M-H] 1063.8.10487] ?H NMR (400 MHz, Chloroform-d) oe 6.36 (dd,J=19.2, 10.3 Hz, 1H), 6.13 (m, 1H), 6.04-5.84 (m, 1H), 5.65(m, 1H), 5.32 (m, 1FI), 6.21 (m, 1FI), 5.11 (m, 1?H), 4.1 (dd,i=13.7, 7.5 Hz, 1H), 4.21-4.03 (m, IH), 3.83 (dd, J=15.2, 5.1Hz, 2H), 3.74 (d, J?=13.2 Hz, 1H), 3.59 (dq, J=10.9, 6.8, 5.6Hz, 2H), 3.52 (d, J=7.1 Hz, 1H), 3.46-3.33 (m, 7H), 3.30 (m,3H), 3.18 (m, 3H), 3.10-2.82 (m, 3H), 2.39 (t, J=4.1 Hz, 1112.28(m,311),2.14(m,3H), 1.90-1.77(m,4H), 1.74(m,4H

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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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(S)-4-Benzylthiazolidine-2-thione, cas is 171877-39-7, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

Add 1000 ml of dichloromethane and 500 ml (3.6 mol) of triethylamine to a 5-liter four-necked flask.Benzylthiooxazolidinone 209g (1mol), phenylacetic acid 140g (1mol),300 g (1 mol) of 2-chloropyridine p-toluenesulfonic acid methyl salt was added dropwise1000 ml of methylene chloride solution, added, and stirred at 25 C for 5 hours.TLC showed complete reaction, adding water to extract the reaction, followed by water,The organic phase is washed with saturated brine, dried over anhydrous sodium sulfate and concentrated.Recrystallization gave 300 g of product with a yield of 91.7%.HPLC purity >99%., 171877-39-7

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Patent; Shanghai Lark Pharmaceutical Technology Co., Ltd.; Shen Xin; Yang Jidong; Hu Xiaochuan; Li Feng; (6 pag.)CN109020913; (2018); 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.

Example 10.Lambdar-[(2,6-Dimethylphenyl)methyl]-6-(l,l-dioxido-2-isothiazolidinyl)-2,3- dimethylimidazo[l,2-alpha]pyridin-8-amine hydrochlorideA mixture of 6-bromo-N-[(2,6-dimethylphenyl)methyl]-2,3-dimethylimidazo[ 1 ,2- alpha]pyridin-8-amine (100 mg, 0.28 mmol; WO 98/37080), isothiazolidine 1,1 -dioxide (67 mg, 0.56 mmol; WO 04/050619), copper(I) iodide (16 mg, 0.083 mmol), potassium carbonate (138 mg, 1.0 mmol) and N,N’-dimethylethylenediamine (7.4 mg, 0.083mmol) in dioxane (2 mL) was heated in an Initiator Microwave Synthesizer at 14O0C for 12 hours. The cooled mixture was applied to an Isolute SCX cartridge. Elution with methanol, followed by water, then methanol then IM NH3 in methanol gave, after evaporation, the product which was further purified by chromatography on EPO silica gel. Elution with dichloromethane/methanol (0 to 10%) gave a pale yellow solid which was dissolved in dichloromethane (2 mL), Ethereal HCl (IM; LOmL) was added and the solvent evaporated. The residue was triturated under ether (1 mL) and filtered to give the title compound as a colourless solid; MS (ES+ve): [M+H]+ at m/z 399 (C2IH26N4O2S requires [M+H]+ at m/z 399).

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Patent; GLAXO GROUP LIMITED; WO2007/3386; (2007); A1;,
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171877-39-7, (S)-4-Benzylthiazolidine-2-thione is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,171877-39-7

General procedure: To thiazolidine-2-thiones (1.0 equiv.) in THF (5.5 mL/mmol), 60% NaH dispersion in mineral oil (1.2 equiv.)was slowly added at 0 C. The reaction mixture was stirred for 15 min at 0 C before acetyl chloride (1.2 equiv.)was added dropwise. The reaction mixture was stirred for 30 min at 0 C, upon which it was warmed to roomtemperature and allowed to stir for another 2 h. The reaction was quenched with saturated NH4Cl (3 mL/mmol)and the layers were separated. The aq. layer was extracted with EtOAc (2 x 4 mL/mmol) and the combinedorganic layers were dried (Na2SO4),filtered, and concentrated in vacuo. The crude product was purified bycolumn chromatography on silica (hexanes/EtOAc 8:2) to afford the title compounds as yellow oils.

171877-39-7 (S)-4-Benzylthiazolidine-2-thione 11458470, athiazolidine compound, is more and more widely used in various fields.

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Article; Tungen, J¡ãrn E.; Aursnes, Marius; Hansen, Trond Vidar; Tetrahedron Letters; vol. 56; 14; (2015); p. 1843 – 1846;,
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5908-62-3, 1,1-Dioxo-isothiazolidine is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,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)+.

As the paragraph descriping shows that 5908-62-3 is playing an increasingly important role.

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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;,
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