Heterocyclic Building Blocks-Isothiazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.677304-75-5,6-Bromobenzo[d]isothiazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

677304-75-5, The following procedure was used to prepare benzisothiazole tert-butyl esters: Di-tert-butyldicarbonate (128 mmol) was added to a suspension of 6-bromo-1,2-benzisothiazole-3-carboxylic acid (46.5 mmol) and 4-dimethylaminopyridine (4.26 mmol) in tert-butyl alcohol (40.0 mL) and tetrahydrofuran (40.0 mL) and the reaction mixture was heated at 65 C. for 16 hours. There was vigorous carbon dioxide evolution which gradually subsided as the mixture become homogeneous. The reaction mixture was concentrated and the residue was dissolved in dichloromethane. The dichloromethane solution was filtered through silica gel (ca. 50 g) and the eluent was concentrated to provide the ester product in 99% yield.

The synthetic route of 677304-75-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Schumacher, Richard; Danca, Mihaela Diana; Ma, Jianguo; Herbert, Brian; Nguyen, True Minh; Xie, Wenge; Tehim, Ashok; US2007/78147; (2007); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

A common heterocyclic compound, the isothiazole compound, name is 2,3-Dihydrobenzo[d]isothiazole 1,1-dioxide,cas is 936-16-3, mainly used in chemical industry, its synthesis route is as follows.,936-16-3

To a solution of {5-(4-fluorophenyl)-1-isobutyl-1H-pyrazol-3-yl}methanol (19.4 mg, 0.078 mmol) in methylene chloride (1 mL) were added PPh3 (42.8 mg, 0.163 mmol) and CBr4 (66.3 mg, 0.200 mmol) at 0¡ã C., followed by stirring at the same temperature for 30 minute to give {5-(4-fluorophenyl)-1-isobutyl-1H-pyrazol-3-yl}methyl bromide. When the reaction was completed as measured by TLC (Hexane:EtOAc=2:1), drops of 1,2-benzisothiazoline-1,1-dioxide (24.3 mg, 0.078 mmol) N,N-dimethylformamide (1.5 mL) were slowly added to the solution. (0338) Then, potassium carbonate (113 mg, 0.816 mmol) were added at the same temperature, and the resulting solution was stirred for a day. When the reaction was completed as measured by TLC (Hexane:EtOAc=2:1), water was added, after which extraction was carried out with ethyl acetate and brine. The organic layer thus formed was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The concentrate was purified by column chromatography (Hexane:EtOAc=2:1) to afford the title compound (19.2 mg, 62percent percent, white solid). (0339) M.P. 110.8-118.2¡ã C.; (0340) 1H NMR (300 MHz, CDCl3) delta 7.61-7.52 (m, 2H), 7.46-7.33 (m, 4H), 7.18-7.12 (m, 2H), 6.41 (s, 1H), 4.56 (s, 2H), 4.41 (s, 2H), 3.91 (d, J=7.5 Hz, 2H), 2.26-2.08 (m, 1H), 0.80 (d, J=6.7 Hz, 6H); (0341) 13C NMR (75 MHz, CDCl3) delta 146.0, 144.5, 136.8, 135.2, 134.0, 133.0, 132.6, 131.0, 130.8, 129.2, 129.1, 124.8, 124.5, 121.4, 115.9, 115.6, 106.3, 56.7, 49.9, 45.7, 41.2, 29.6, 19.8

As the rapid development of chemical substances, we look forward to future research findings about 936-16-3

Reference£º
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; NAM, Ghil Soo; CHOI, Kyung Il; KIM, Jung Hyun; PAE, Ae Nim; HONG, Jin Ri; LEE, Jae Kyun; (30 pag.)US2015/329533; (2015); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

A common heterocyclic compound, the isothiazole compound, name is 2,3-Dihydrobenzo[d]isothiazole 1,1-dioxide,cas is 936-16-3, mainly used in chemical industry, its synthesis route is as follows.,936-16-3

Step 2. A mixture of 12 (100 mg, 0.40 mmol), 1 (67 mg, 0.40 mmol), potassium carbonate (55 mg, 0.40 mmol), Cul (3.8 mg, 0.019 mmol), and L-proline (2.3 mg, 0.019 mmol) in dioxane (4 mL) was stirred at 110¡ãC for 16 hours under an inert atmosphere. Upon completion, water (40 mL) was added and the reaction mixture was extracted with EtOAc (90 mL). The organic phase was washed with brine (50 mL) and concentrated under reduced pressure. Purification with prep-HPLC (0.075percent TFA/CH3CN/H20 system) resulted in Compound 121 (40 mg, 29percent) as yellow solid and TFA salt. 1H NMR (DMSO-d6, 400MHz) delta 8.69-8.68 (d, 1H), 8.53-8.52 (d, 1H), 7.99-7.94 (m, 3H), 7.77 (m, 1H), 7.67-7.62 (m, 3H), 7.07-7.05 (d, 1H), 6.83-6.81 (d, 1H), 4.95 (s, 2H); LCMS (ESI): m/z 340.1 (M+H).

As the rapid development of chemical substances, we look forward to future research findings about 936-16-3

Reference£º
Patent; NUMERATE, INC.; RAIMUNDO, Brian; KOLTUN, Elena S.; GRIFFIN, John; STANGELAND, Eric; (93 pag.)WO2018/49324; (2018); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.936-16-3,2,3-Dihydrobenzo[d]isothiazole 1,1-dioxide,as a common compound, the synthetic route is as follows.,936-16-3

Example 84 2-[{1-(tert-Butyl)-5-isobutyl-1H-pyrazol-3-yl}methyl]-2,3-dihydro[d]isothiazole 1,1-dioxide (Compound 29) To a solution of 1,2-benzisothiazoline-1,1-dioxide (70.4 mg, 0.416 mmol) in N,N-dimethylformamide (2 mL) was added potassium carbonate (578 mg, 4.16 mmol) at room temperature, followed by stirring for 10 min. This solution was slowly added with drops of {1-(tert-butyl)-5-isobutyl-1H-pyrazol-3-yl}methyl bromide (126 mg, 0.462 mmol) in methylene chloride (4 mL), and then stirred at room temperature for a day. When the reaction was completed as measured by TLC (Hexane:EtOAc=6:1), the reaction mixture was filtered through celite in vacuo. The filtrate was neutralized with 1M HCl and an aqueous saturate sodium hydrogen carbonate solution. After extraction with ethyl acetate and water, the organic layer thus formed was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The concentrate was purified by column chromatography (Hexane:EtOAc=6:1) to afford the title compound (124 mg, 79percent, white solid). M.P. 102.5-105.4¡ã C.; 1H NMR (300 MHz, CDCl3) delta 7.81 (d, J=6.6 Hz, 1H), 7.60-7.48 (m, 2H), 7.36 (d, J=7.4 Hz, 1H), 6.18 (s, 1H), 4.45 (s, 2H), 4.34 (s, 2H), 2.64 (d, J=7.1 Hz, 2H), 2.06-1.09 (m, 1H), 1.64 (s, 9H), 0.98 (d, J=6.6 Hz, 6H); 13C NMR (75 MHz, CDCl3) delta 143.62, 143.10, 135.4, 134.3, 132.5, 128.9, 124.5, 121.3, 106.7, 59.9, 49.9, 41.5, 37.3, 30.5, 28.4, 22.7

The synthetic route of 936-16-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; NAM, Ghil Soo; CHOI, Kyung Il; KIM, Jung Hyun; PAE, Ae Nim; HONG, Jin Ri; LEE, Jae Kyun; (30 pag.)US2015/329533; (2015); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

10271-85-9, Isothiazole-5-carboxylic acid is a isothiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 318 (12 mg, 0.029 mmol), isothiazole-5-carboxylic acid (7.38 mg, 0.057 mmol) and triethylamine (7.97 mul, 0.057 mmol) were suspended in toluene (1 mL) in a pressure rated 1 dram vial. Diphenylphosphoryl azide (15.73 mg, 0.057 mmol) was added to the mixture which was heated to 110 C for 3 hours. The crude reaction mixture was purified by reverse phase HPLC (Method D, 65-100% 20 min, 100% 5 min) to yield Example 621 (1.3 mg, 2.38 mmol, 8% yield). C-MS: Method H, RT = 1.25 min, MS (ESI) m/z: 546.10 (M+H)+. 1HNMR (500 MHz, DMSO-d6) delta 8.77 (s, 1H), 8.62 (s, 1H), 8.21 (s, 1H), 8.02-8.12 (m, 1H), 7.88 (s, 1H), 6.81 (s, 1H), 4.61-4.69 (m, 2H), 4.46-4.56 (m, 2H), 4.10 (s, 3H), 3.19 (s, 3H)., 10271-85-9

The synthetic route of 10271-85-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

The isothiazole compound, name is 3-Piperazinobenzisothiazole hydrochloride,cas is 87691-88-1, mainly used in chemical industry, its synthesis route is as follows.,87691-88-1

A mixture of 3-piperazin-1-yl-benzo[d]isothiazole hydrochloride (1.62 g, 6.34 mmol), product from Example 88B (1.90 g, 7.61 mmol), anhydrous potassium carbonate (1.93 g, 13.9 mmol), and potassium iodide (200 mg) in acetonitrile (80 ml) was refluxed for 48 hours. The reaction mixture was concentrated and the residue was partitioned between methylene chloride and water. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The crude product was eluted through a flash column (silica gel 60, 230-400 mesh, EtOAc) to give a clear, viscous oil which crystallized on standing. Yield = 1.16 g (42%); MS(APCI), (M + 1)+ = 433. 1H-NMR (DMSO-d6, delta) 8.03 (d, 2H, J = 9.0 Hz), 7.53 (t, 1H, J =8.1, 7.8 Hz), 7.40 (t, 1H, J = 8.1, 7.3 Hz), 6.87 (d, 2H, J = 7.3 Hz), 3.69 (t, 2H, J = 5.9, 5.9 Hz), 3.26-3.43 (m, 6H), 2.46-2.78 (m, 12H), 1.78 (m, 2H). CHN: calculated for C25H28N4OS; C, 69.41%, H, 6.52%, N, 12.95%; found C, 69.28%, H, 6.60%, N, 12.65%.

As the rapid development of chemical substances, we look forward to future research findings about 87691-88-1

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/26864; (2004); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

936-16-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.936-16-3,2,3-Dihydrobenzo[d]isothiazole 1,1-dioxide,as a common compound, the synthetic route is as follows.

Step 1. To a mixture of 6-methyl-2,4-dichloropyrimidine (162 mg, 0.994 mmol) and 1 (185 mg, 1.1 mmol) in anhydrous CH3CN (4 mL) was added K2CO3 (274 mg, 2 mmol), the mixture was stirred at 80¡ãC for 3 hrs. Concentration under reduced pressure resulted in 11 (130 mg), which was submitted to the next step without further purification.

936-16-3 2,3-Dihydrobenzo[d]isothiazole 1,1-dioxide 13638, aisothiazole compound, is more and more widely used in various fields.

Reference£º
Patent; NUMERATE, INC.; RAIMUNDO, Brian; KOLTUN, Elena S.; GRIFFIN, John; STANGELAND, Eric; (93 pag.)WO2018/49324; (2018); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

24340-77-0, 4-Bromoisothiazole is a isothiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 58: Methyl 6-(benzenesulphonylmethyl)-3-(isothiazol-4-yl)-2-methoxybenzoate[0588] A mixture of methyl 6-(benzenesulphonylmethyl)-2-methoxy-3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (Intermediate 59, 0.15g), tri-tert-butyl- phosphinium tetrafluoroborate (O.Olg), cesium carbonate (0.34g), tris-(dibenzylideneacetone)- dipalladium (0.016g), and 4-bromoisothiazole (0.06g) in dioxane (3.2ml) and water (0.4ml) was degassed and then heated in the microwave at 120C for 20 minutes. After cooling, the mixture was diluted with ether, dried (MgS04) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60% to give crude methyl 6- (benzenesulphonylmethyl)-3-(isothiazol-4-yl)-2-methoxy-benzoate (0..044g) as an oil. The material was used without further purification or characterisation.

24340-77-0, The synthetic route of 24340-77-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ZAFGEN CORPORATION; DYKE, Hazel, Joan; CRAMP, Susan, Mary; PALLIN, Thomas, David; KULAGOWSKI, Janusz, Jozef; MONTANA, John, Gary; ZAHLER, Robert; WO2011/44506; (2011); A2;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

27148-03-4, Benzo[d]isothiazole-3(2H)-thione 1,1-dioxide is a isothiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

27148-03-4, General procedure: Thiosaccharin (Htsac) (0.070 g, 0.353 mmol) in MeOH (5 cm3)was added to a suspension of 1 (0.150 g, 0.353 mmol) in CHCl3(8 cm3). The mixture was stirred for 3 h and refluxed on a steambath for 10 min. The orange-red solid thus formed was collected,washed with EtOH and dried in a vacuum oven (yield: 0.128 g,79%). Anal. Calc. for C14H8N2O3PdS3: C, 36.97; H, 1.77; N, 6.16.Found: C, 37.12; H, 1.96; N, 6.30%. IR (KBr); 3049w, 1632s,1562m, 1443m, 1423m, 1016m, 804m, 439m, 413m cm1. 1HNMR (d6-dmso): d 7.95 (d, J 8.1, 1H, tsac), 7.89-7.73 (m, 5H, tsac& bit), 7.6 (t, J 7.5, 1H, bit), 7.41 (t, J 7.5, 1H, bit) ppm.Decomposes at 282 C.

The synthetic route of 27148-03-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Al-Jibori, Subhi A.; Ahmed, Birgul S.M.; Ahmed, Safaa A.; Karada?, Ahmet; Schmidt, Harry; Wagner, Christoph; Hogarth, Graeme; Inorganica Chimica Acta; vol. 436; (2015); p. 7 – 15;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

7716-66-7, 3-Chlorobenzo[d]isothiazole is a isothiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7716-66-7, A solution of 3-chlorobenzo[d]isothiazole (1.0 g, 5.9 mmol) in chlorosulfonic acid (2 mL) was heated at 150 “C for 2.5h. The resulting reaction mixture was then cooled to room temperature and thionyl chloride (0.9 mL, 12.3 mmol) was added. The resulting yellow solution was heated at 150 “C for 2h, allowed to cool to room temperature and poured over ice. The aqueous reaction mixture was then extracted with ethyl acetate, dried over EPO anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a pale yellow oil which crystallized into an off-white solid upon standing at -20 0C (1.43 g). MW=267 confirmed by LC-MS, t,.= 4.17 min (Method B) MH+=268.

As the paragraph descriping shows that 7716-66-7 is playing an increasingly important role.

Reference£º
Patent; RIGEL PHARMACEUTICALS, INC.; WO2006/91858; (2006); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com