Heterocyclic Building Blocks-Thiazolidine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1438-16-0,3-Aminorhodanine,as a common compound, the synthetic route is as follows.

The 3-amino-2-thioxothiazolidin-4-one (2, 3-amino-rhodanine,302.2 mg, 2.04 mmol) in ethanol (15 mL) was heated to boiling for10 min, and the solution of indoline-2,3-dione (1, isatin, 300.0 mg,2.04 mmol) in ethanol (15 mL) was added slowly using dropwise. Thereaction mixture was stirred for 5 h at 100 C without catalyst, and wasmonitored by TLC. After the completion of the reaction, the red productformed was recrystallized from ethanol, filtered, and dried in vacuo.After recrystallization, 2-OxI-Rh (407 mg, 72%), which is Z isomer, wasobtained as red solid (m.p. > 300 C). 1H-NMR (400 MHz, DMSO-d6):delta 11.25 (s, NH, 1 H), 8.82 (d, J =7.7 Hz, =CH, 1 H), 7.42 (t, J=7.7 Hz, =CH, 1 H), 7.10 (t, J =7.7 Hz, =CH, 1 H), 6.97 (d, J=7.7 Hz, =CH, 1 H), 5.97 (bs, NH2, 2 H); 13C-NMR (100 MHz, DMSOd6):delta 191.9, 168.0, 163.5, 144.8, 133.2, 128.6, 127.8, 125.5, 122.2,119.9, 110.7 (Fig. S1); IR (KBr, cm-1): 3410 cm-1 (NH2, stretch primary),3146 cm-1 (]CeH, isatin H), 1713 cm-1 (C]O), 1632 cm-1(O]C-NeC]S), 1595 cm-1 (CeC, stretch in ring), 1458, 1335 cm-1(C]S), 1189 cm-1 (CeN, stretch peak), 742 cm-1 (NH2 wag) (Fig. S2);Anal. Calcd. for C11H7N3O2S2: C, 47.64; H, 2.54; N, 15.15; O, 11.54; S,23.12; found: C, 47.57; H, 2.31; N, 15.07

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

Reference£º
Article; Bayindir, Sinan; Journal of Photochemistry and Photobiology A: Chemistry; vol. 372; (2019); p. 235 – 244;,
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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.

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.

With the rapid development of chemical substances, we look forward to future research findings about 7025-19-6

Reference£º
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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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.

Example 60: 5-{5-[(3-{(1R,5S/1S,5R)-1-[4-(1,1-Dioxido-2-isothiazolidinyl)phenyl]-3- azabicyclo [3. 1.0] hex-3-yl} propyl) thio]-4-methyl-4H-1, 2, 4-triazol-3-yl}-2- methylquinoline hydrochloride; A Schlenk tube was charged with 5-[5-({3-[(1R,5S/1S,5R)-1-(4-bromophenyl)-3- azabicyclo [3.1. 0] hex-3-yl] propyl} thio)-4-methyl-4H-1, 2, 4-triazol-3-yl]-2-methylquinoline (cf. Example 2; 0.15 g), isothiazolidine 1,1-dioxide (46 mg), tris (dibenzylideneacetone)- dipalladium (0) (6 mg), 4,5-bis (diphenylphosphino)-9, 9-dimethylxanthene (10 mg), cesium carbonate (130 mg) and 1,4-dioxane (2 mL). The Schlenk tube was sealed with a teflon screwcap and the reaction mixture was stirred at 100 C for 12 h. The reaction mixture was allowed to cool to room temperature, diluted with dichloromethane (10 mL), filtered and concentrated in vacuo. The crude product was purified by flash chromatography (dichloromethane to 10% MeOH in dichloromethane) to give 50 mg of the free base of the title compound. To a solution of this material in dichloromethane (0.3 mL) was added HCI (0.087 mL, 1 M in Et20), the solvent evaporated in vacuo and the material thus obtained triturated with Et20 to give 52 mg of the title compound as a white solid. NMR (‘H, DMSO): 8 10.57 (bs, 1H), 8.27 (bd, 1H), 8.19 (d, 1H), 7.94 (t, 1H), 7.82 (d, 1H), 7.55 (d, 1H), 7.32 (d, 2H), 7.18 (d, 2H), 4.03 (dd, 1H), 3.72 (m, 3H), 3.60/3. 20 (bm, 8H), 3.45 (s, 3H), 2.75 (s, 3H), 2.41 (m, 2H), 2.25 (m, 2H), 2.14 (m, 1H), 1.66/1. 10 (t/m, 2H). MS (m/z) : 575 [MH] +.

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

Reference£º
Patent; GLAXO GROUP LIMITED; WO2005/80382; (2005); A1;,
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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

(1S,2S)-N1,N2-Dimethylcyclohexane-1,2-diamine (46.1 mg, 0.30 mmol) and copper iodide (56.3 mg, 0.30 mmol) were added to a mixture of 2,3-dichloro-5-nitropyridine (571 mg, 2.96 mmol), isothiazolidine 1,1-dioxide (430 mg, 3.55 mmol) and potassium carbonate (817.5 mg, 5.92 mmol) in dioxane (6 mL) under N2. The reaction mixture was stirred at 100 C. for 16 h. The mixture was filtered, and the filtrate was extracted with ethyl acetate. The organic extracts were dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The resultant crude product was purified by flash chromatography (petroleum ether/ethyl acetate=100:0 to petroleum ether/ethyl acetate=50:50) to afford compound 58a as a white solid (600 mg, 73%).

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

Reference£º
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); 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.

EXAMPLE 24; 3,3-Difluoro-cyclobutanecarboxylic Acid ((S)-3-{5-[2-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)-4,6-dimethyl-pyrimidine-5-carbonyl]-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl}-1-phenyl-propyl)-amide (I-49); step 1-; A solution of isothiazolidine 1,1-dioxide (114, 40 mg, 0.33 mmol; CAS Reg No. 5908-62-3) in THF (0.4 mL) and DMF (0.4 mL) was treated with NaH (14 mg, 60% dispersion in mineral oil) and heated to 80 C. for 5 min before a solution of 84 (116 mg, 0.27 mmol) in DMF (1.6 mL) was added. The reaction mixture was stirred at 80 C. for 5 min, allowed to cool to RT, quenched by the addition of water, extracted with EtOAc, dried (Na2SO4) and concentrated in vacuo. The residue was purified by SiO2 column chromatography eluting with DCM:MeOH:NH4OH (60/10/1) to afford 115 mg (90%) of 115a.

With the rapid development of chemical substances, we look forward to future research findings about 5908-62-3

Reference£º
Patent; Lemoine, Remy; Melville, Chris Richard; Rotstein, David Mark; Wanner, Jutta; US2007/191335; (2007); A1;,
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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

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.

1438-16-0 3-Aminorhodanine 74033, athiazolidine compound, is more and more widely used in various.

Reference£º
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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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

To a solution (45r)-4-benzyl-l,3-thiazolidine-2-thione (38 g) in dichloromethane (350 mL), cooled to O0C was added propylene oxide (12.7 mL) and trifluoroacetic acid (14 mL). After stirring the reaction mixture for 2 hours, the solvents were evaporated under reduced pressure to obtain a residue which was purified by column chromatography over silica gel using 20% ethylacetate in hexane as eluant to afford the title compound (0.9 g). Mass (m/z): 194.18

As the paragraph descriping shows that 171877-39-7 is playing an increasingly important role.

Reference£º
Patent; RANBAXY LABORATORIES LIMITED; WO2008/23336; (2008); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1438-16-0,3-Aminorhodanine,as a common compound, the synthetic route is as follows.

53 Sodium borohydride (19.1 g) was added to 48 THF (750 mL), and slurry of 54 N-aminorhodanine (250 g) in THF (500 mL) was added portionwise at below 5 C. After stirring for 30 minutes at below 5 C., 55 methanol (111 mL) was added dropwise, and the mixture was stirred for 2 hours. 56 Conc. hydrochloric acid (44 mL) was diluted with water (500 mL) and added dropwise to the mixture, and then 49 water (1000 mL) was added dropwise, and the mixture was stirred for 1 hour at below 10 C. The precipitated crystals were filtered, washed with water (600 mL) and dried at 40 C. under reduced pressure to yield the 57 title compound (209.1 g). (0189) MS (m/z): 151 [M+H]+

As the paragraph descriping shows that 1438-16-0 is playing an increasingly important role.

Reference£º
Patent; NIPPON SHINYAKU CO., LTD.; HIGUCHI, Fumi; (17 pag.)US2019/48023; (2019); A1;,
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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

A mixture of 5-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[l,2,3]triazolo[4,5-d] pyrimidine (15.9 mg, 47.2 muiotaetaomicron?), 1,1-dioxo-isothiazolidine (11.4 mg, 94.4 muiotaetaomicron?) and DBU (14.2 mu?^, 94.4 mumol) in DMF (250 mu?) was stirred at the room temperature overnight. The reaction mixture was directly purified by preparative HPLC (column: Gemini 5um C18 110A 75 x 30mm. mobile phase: water (0.05% Et3N): acetonitrile 75:25% to 5:95%. WL: 230 nm Flow: 30 mL/min.) to afford the title compound as white solid (3.10 mg, 16%). MS(m/e): 387.3 (MH+).

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; ADAM, Jean-Michel; BISSANTZ, Caterina; GRETHER, Uwe; KIMBARA, Atsushi; NETTEKOVEN, Matthias; ROEVER, Stephan; ROGERS-EVANS, Mark; WO2013/68306; (2013); 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.

To a stirred solution of 5-{9-fluoro-6-methanesulfonyl-5-[(S)-oxan-4- y l(pheny l)methy 1] -5H-py rido [3,2-b] indol-3 -y 1 } – 1 ,4-dimethy 1- 1H- 1 ,2,3-triazole (25.0 mg 0.0500 mmol) and isothiazolidine-l,l-dione (5.7 mg, 0.0500 mmol) in DMF (0.25 mL) was added t-BuOK (21.0 mg, 0.190 mmol). This mixture was heated at 65 C for 1.5 h and cooled to room temperature. The mixture was then diluted with MeOH and purified via preparative LC/MS with the following conditions: Column: Waters XBridge Phenyl, 19 x 200 mm, 5-mutaueta particles; Mobile Phase A: 5:95 ACN: water with 10 mM NH4OAC; Mobile Phase B: 95:5 ACN: water with 10 mM NH4OAc; Gradient: 15-70% B over 20 min, then a 5-min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give 2-[3-(dimethyl-lH- l,2,3-triazol-5-yl)-6-methanesulfonyl-5-[(S)-oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2- b]indol-9-yl]- 6,2-thiazolidine-l,l-dione (12.3 mg, 41%). NMR (500MHz, DMSO- de) delta 8.72 (s, IH), 8.38 (d, J=8.4 Hz, IH), 7.88 (s, IH), 7.62 (br d, J=8.4 Hz, 3H), 7.36- 7.30 (m, 2H), 7.27 (br d, J=7.1 Hz, IH), 6.81 (br d, J=10.1 Hz, IH), 4.11 (br d, J=2.0 Hz, 2H), 3.86 (br d, J=9.8 Hz, IH), 3.76 (s, 3H), 3.74 (s, 2H), 3.64 (br d, J=8.8 Hz, IH), 3.57 (br t, J=7.4 Hz, IH), 3.19 (br t, J=12.1 Hz, IH), 2.65-2.57 (m, 2H), 2.54 (s, 3H), 2.07 (s, 3H), 1.95 (br d, J=12.5 Hz, IH), 1.75-1.56 (m, 2H), 0.42 (br d, J=12.1 Hz, IH). LCMS: RT = 1.414 min; (ES): m/z (M+H)+ = 634.95; LCMS: Column: Waters Acquity UPLC BEH C18, 2.1 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 5:95 ACN:water with 10 mM NH4OAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH4OAC; Temperature: 50 C; Gradient: 0-100% B over 3 min, then a 0.75-min hold at 100% B; Flow: 1.11 mL/min. HPLC Purity at 220 nm: 100 %

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

Reference£º
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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