Month: September 2020

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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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 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 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 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 5908-62-3 name is 1,1-Dioxo-isothiazolidine, mainly used in chemical industry, its synthesis route is as follows.

5908-62-3, A 50 ml flask was charged under nitrogen with 3-bromo-5-nitro-benzoic acid methyl ester (D11) (1 g, 3.8 mmol, 1 equiv), Cs2CO3 (536 mg, 4.4 mmol, 1.2 equiv) tris (DIBENZYLIDENEACETONE) DIPALLADIUM (0) (5 mg, 0.0055 mmol, 0.0154 equiv), Xantphos (10 mg, 0.014 mmol, 0.04 equiv) and toluene (15 ML). Isothiazolidine 1,1-dioxide (D22a) (536 mg, 4.4 mmol, 1.1 equiv) was then added and the resulting mixture was stirred at 90C for 16 hours then cooled to room temperature and diluted with H20 and AcOEt. The layers were separated, the aqueous phase diluted with a saturated aqueous NAHC03 solution and extracted with AcOEt. The combined organic phases were dried over MGS04 and concentrated in vacuo to give 3- (1, 1-DIOXO-116-ISOTHIAZOLIDIN-2-YL)-5-NITRO-BENZOIC acid methyl ester (D15) (187 mg, 16%) as a yellow solid. [M+H+NH3] + = 318.0, RT = 2. 81 min

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Patent; GLAXO GROUP LIMITED; WO2004/50619; (2004); A1;,
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The thiazolidine compound, cas is 26364-65-8 name is 2-Cyanoimino-1,3-thiazolidine, mainly used in chemical industry, 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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The thiazolidine compound, cas is 7025-19-6 name is 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, mainly used in chemical industry, its synthesis route is as follows.

7025-19-6, General procedure: 0.005 mol of appropriate rhodanine-3-alkanoicacid, 5 g molecular sieves 4 A, 25 cm3 isopropyl alcohol,0.0055 mol appropriate aldehyde and 2.53 g (0.025 mol)triethylamine were placed in a flask. The mixture washeated under a reflux condenser for 5 h in nitrogen. Afterheating, the solution was filtered hot. The permeate wascooled and 50 cm3 of 2M hydrochloric acid solution wasadded. The resulting sediment was filtered using Buechnerfunnel and crystallised from isopropyl alcohol or glacialacetic acid.

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Article; Tejchman, Waldemar; Korona-Glowniak, Izabela; Malm, Anna; Zylewski, Marek; Suder, Piotr; Medicinal Chemistry Research; vol. 26; 6; (2017); p. 1316 – 1324;,
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1438-16-0, 3-Aminorhodanine is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1438-16-0

General procedure: To a reaction vessel was added compound19(70 mg, 0.16 mmol), thiazolidine-2,5-dione (28 mg, 0.25 mmol), piperidine (2 muL, 0.02 mmol) and acetic acid (1 muL, 0.02 mmol) in the presence of toluene. The reaction mixture was refluxed overnight and the reaction solvent was removed by evaporation. The residual was dissolved in EtOAc and washed with H2O (2 x 10 mL) and brine. The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purifiedby silica gel column chromatography using 20% EtOAc in hexanes to afford compound20(57 mg, 66%).

The synthetic route of 1438-16-0 has been constantly updated, and we look forward to future research findings.

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Article; Kim, Hyojin; Cho, Suk Joon; Yoo, Minjin; Kang, Seung Kyu; Kim, Kwang Rok; Lee, Hwan Hee; Song, Jin Sook; Rhee, Sang Dal; Jung, Won Hoon; Ahn, Jin Hee; Jung, Jae-Kyung; Jung, Kwan-Young; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5213 – 5220;,
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The thiazolidine compound, cas is 7025-19-6 name is 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, mainly used in chemical industry, its synthesis route is as follows.

7025-19-6, [00161] To a solution of 2,3-dimethoxybenzaldehyde 1 (200 mg, 1.20 mmol) and 3-(4- oxo-2-thioxothiazolidin-3-yl)propanoic acid 2 (247 mg, 1.20 mmol) in glacial acetic acid (4 mL) was added sodium acetate (197 mg, 2.41 mmol) and the reaction was heated at 90 C for 6 h. After the completion of reaction (as monitored by LCMS) the reaction mixture was poured into ice cooled water, stirred for 15 mm and the solid precipitated out was filtered, washed with diethyl ether and dried in vacuo to afford 235 mg (55% yield) of NADi-241 as yellow solid. ?H NMR (400 MHz, DMSO-d6) 12.50 (s, 1 H), 7.89 (s, 1 H), 7.25 (d, J = 1.87 Hz, 2 H), 7.06 (dd, J = 3.74, 5.62 Hz, 1 H), 4.20 – 4.26 (m, 2 H), 3.86 (s, 3 H), 3.82 (s, 3 H), 2.61 – 2.66 (m, 2 H) ; MS (ES+): mlz = 353.90 [M+Hj; HPLC = 99.28%.

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Patent; UNIVERSITY OF MIAMI; UNIVERSITY OF MARYLAND, BALTIMORE; SPYVEE, Mark; CAPOBIANCO, Anthony, J.; MACKERELL, Alex, Jr.; (114 pag.)WO2016/154255; (2016); A1;,
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