Heterocyclic Building Blocks-Isothiazole

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

General procedure: Potassium carbonate was dissolved in DMF, and 1,2-bezeneisothiazolin-1,1-dioxide (8) (1 equiv.) in dichloromethanewas added to the reaction solution, and stirred for overnight. Then,the reaction mixture was filtered through Celite, and washed with1 N HCl and saturated sodium hydrogen carbonate solution. Residualsolution was dried over magnesium sulfate, and concentratedin vacuo, and purified by column chromatography to afford the titlecompound.

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Reference£º
Article in Press; Hong, Jin Ri; Choi, Young Jin; Keum, Gyochang; Nam, Ghilsoo; Bioorganic and Medicinal Chemistry; (2017);,
Isothiazole – Wikipedia
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A common heterocyclic compound, the isothiazole compound, name is Isothiazole,cas is 288-16-4, mainly used in chemical industry, its synthesis route is as follows.,288-16-4

EXAMPLE 1 alpha,alpha-Bis(4-chlorophenyl)-5-isothiazolemethanol To a solution of 1.0 g of isothiazole in 20 ml of tetrahydrofuran were added 8.1 ml of a 1.52M solution of n-butyllithium in hexane at -78 C. The mixture was allowed to stir for 15 minutes at which time 3.2 g of 4,4′-dichlorobenzophenone were added as a solution in 25 ml of tetrahydrofuran. The reaction was allowed to warm to room temperature and was stirred for 2 hours. Twenty-five milliliters of a saturated ammonium chloride solution were added and the tetrahydrofuran was removed by evaporation. The resulting mixture was extracted three times with ethyl acetate. The combined organic extracts were washed with a saturated ammonium chloride solution, water, and a saturated sodium chloride solution, dried over magnesium sulfate and evaporated. The resulting oil was chromatographed over silica gel. The appropriate fractions were combined and evaporated resulting in an oil. Cyclohexane was added and 1.21 g of the desired title product were recovered by filtration as white crystals, m.p. 118-119.5 C. Analysis for C16 H11 Cl2 NOS: Calc.: C, 57.15; H, 3.30; N, 4.17; Found: C, 57.17; H, 3.07; N, 4.17.

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Reference£º
Patent; Eli Lilly and Company; US4560695; (1985); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18480-53-0,3,4-Dichloroisothiazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.,18480-53-0

To a solution of S^-dichloroisothiazole-delta-carboxylic acid (4.0Og, 20.1 mmol) in dichloromethane (75 ml_), cooled with an ice-brine bath, was added N,N-dimethylformamide (78 mul_, 1 mmol) followed dropwise by oxalyl chloride (1.94 ml_, 22.2 mmol). After stirring at room temperature for 2h, meanwhile gas evolution had completely stopped, all volatiles were removed in vacuo to affor the crude acid chloride (4.30 g).

18480-53-0 3,4-Dichloroisothiazole-5-carboxylic acid 49837, aisothiazole compound, is more and more widely used in various fields.

Reference£º
Patent; BAYER CROPSCIENCE SA; WO2009/130193; (2009); A1;,
Isothiazole – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.822-82-2,Isothiazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.,822-82-2

To a solution of l-[(5R)-4-[methyl(tetrahydropyran-4-yl)amino]-5-oxido-6,7- dihydrothieno[3,2-d]pyrimidin-5-iunn-2-yl]azetidin-3-ol (2.5 g, 7.4 mmol) in DCM (50 mL) was added 4-isothiazolecarboxylic acid ( 1.2 g, 9.6 mmol), DMAP (90 mg, 0.74 mmol) and EDAC ( 1.8 g, 9.6 mmol). The mixture was stirred at room temperature overnight before it was concentrated in vacuo. The residue was purified by column chromatography (DCM/MeOH gradient 20 : 1 to 10 : l(Rf= 0.47 (MeOH/DCM 1 : 10))) and subsequently crystallized twice from n-butyl acetate. The title compound was obtained as colorless crystalline material. 1H NMR (DMSO-d6) delta: 9.81 (s, 1H), 8.99 (s, 1H), 5.59 – 5.38 (m, 1H), 4.94 – 4.75 (m, 1H), 4.47 (dd, J = 10.4, 6.6 Hz, 2H), 4.21 – 4.05 (m, 2H), 4.04 – 3.88 (m, 2H), 3.56 – 3.33 (m, 3H), 3.27 – 3.13 (m, 4H), 3.10 – 2.93 (m, 2H), 1.95 – 1.75 (m, 2H), 1.71 – 1.48 (m, 2H). HPLC-Retention time (XE Metode 7 CM) : 1.89 minutes. Detected “M + l”-mass: 450.12.

The synthetic route of 822-82-2 has been constantly updated, and we look forward to future research findings.

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Patent; LEO PHARMA A/S; LARSEN, Jens; (110 pag.)WO2019/57806; (2019); A1;,
Isothiazole – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18480-53-0,3,4-Dichloroisothiazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.

3,4-Dichloroisothiazole-5-carboxylic acid (CAS 18480-53-0, 34.8 mg, 0.18 mmol) was dissolved in DMF (200 iL). HBTU (83 mg, 0.22 mmol) and TEA (61.1 iL, 0.44 mmol) were added. The solution was stirred for 6 mm and then 4-(2-amino-3-methylbutanoyl)benzonitrile hydrochloride (Example 49b, 35 mg, 0.15 mmol) in DMF (400 iL) and TEA (61.1 iL, 0.44 mmol) was added. The reaction mixture was stirred at rt for 1 h and then purified by preparative HPLC to give 3,4-dichloro-N-(1-(4-cyanophenyl)-3-methyl-1-oxobutan-2-yl)isothiazole-5-carboxamid (15 mg, 28percent).1H NMR (500 MHz, CDCI3) 5 ppm 0.87 (d, 3 H) 1.12 (d, 3 H) 2.26 – 2.36 (m, 1 H) 5.75 (dd, 1 H)7.74 (d, 1 H) 7.86 (d, 2 H) 8.12 (d, 2 H).MS (ESI) m/z 379.7 [M-H], 18480-53-0

As the paragraph descriping shows that 18480-53-0 is playing an increasingly important role.

Reference£º
Patent; ACTURUM LIFE SCIENCE AB; LINDE, Christian Erik; PAULSEN, Kim; SOHN, Daniel; SVENSSON, Mats A; VALLIN, Karl S A; WEIGELT, Dirk; MINIDIS, Alexander; WO2014/184235; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7716-66-7,3-Chlorobenzo[d]isothiazole,as a common compound, the synthetic route is as follows.

7716-66-7, PREPARATION 3 3-(1-Piperazinyl)-1,2-benzisothiazole ¡¤ hydrochloride Anhydrous piperazine (49.4 g, 0.57 mol) and t-butanol (10 mL) were added to a dry, 300 mL round bottom flask equipped with a mechanical stirrer, thermometer, condenser topped with a nitrogen inlet, and pressure-equalizing dropping funnel. After the flask was purged with nitrogen, it was heated to 100 C. in an oil bath. A solution of 3-chloro-1,2-benzisothiazole (19.45 g, 0.11 mol) in t-butanol (10 mL) was added to the addition funnel, and then slowly added to the reaction flask over 20 minutes to moderate an exothermic reaction (112-118 C.). Once addition was complete the yellow solution was heated to reflux (121 C.) and then maintained at reflux for 24 hours. Thin-layer chromatography showed that the reaction was complete. The reaction mixture was cooled to 85 C. and 120 mL of water was added. The hazy solution was filtered and the filter cake rinsed with 60 mL of t-butanol/water (1:1) solution. The pH of the combined filtrate and wash was adjusted to 12.2 with 50% aqueous caustic. The aqueous solution was extracted with toluene (200 mL), the layers were separated, and the aqueous layer was extracted with fresh toluene (100 mL). The combined toluene layers were washed with water (75 mL), and then the toluene solution was concentrated in vacuo at 48 C. to 90 mL. Isopropanol (210 mL) was added to the concentrate and then the pH was slowly adjusted to 3.8 with 7.6 mL of concentrated hydrochloric acid. The resulting slurry was cooled to 0 C., granulated for 45 min, and then filtered. The filter cake was washed with cold isopropanol (50 mL) and then dried in vacuo at 40 C. to afford 23.59 g (80% yield) of 3-(1-piperazinyl)-1,2-benzisothiazole hydrochloride as an off white solid.

7716-66-7 3-Chlorobenzo[d]isothiazole 598190, aisothiazole compound, is more and more widely used in various fields.

Reference£º
Patent; Pfizer Inc.; US5935960; (1999); A;,
Isothiazole – Wikipedia
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A common heterocyclic compound, the isothiazole compound, name is 3,4-Dichloroisothiazole-5-carboxylic acid,cas is 18480-53-0, mainly used in chemical industry, its synthesis route is as follows.,18480-53-0

Preparation of the Starting Material At room temperature, 146 g (1.23 mol) of thionyl chloride are added dropwise with stirring over a period of 5 minutes to 8.92 g (0.045 mol) of 3,4-dichloro-isothiazole-5-carboxylic acid. Four drops of dimethylformamide are then added and the reaction mixture is heated under reflux for one hour. The reaction mixture is subsequently cooled to room temperature and concentrated under reduced pressure. In this manner, 12.19 g of 3,4-dichloro-isothiazole-5-carbonyl chloride are obtained in the form of an orange oil.

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Reference£º
Patent; Bayer Aktiengesellschaft; US6277791; (2001); B1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.24340-77-0,4-Bromoisothiazole,as a common compound, the synthetic route is as follows.

To a reaction flask were added compound 41 (100 mg, 0.19 mmol), 4-bromoisothiazole (50 mg, 0.27 mmol), Pd(dppf)Cl2 (5 mg, 0.006 mmol) and sodium carbonate (60 mg, 0.558 mmol), 5 mL glycol dimethyl ether and 0.9 mL water were added, bubbled with nitrogen gas for 10 minutes, and the reaction was heated to 100 C in microwave and reacted for half an hours. After TLC detected the reaction was complete, the reaction was concentrated, purified by silica gel column chromatography to afford 58 mg of a product, yield: 63%. LC-MS(APCI): m/z = 485.3 (M+1)+. 1H NMR (400 MHz, CDCl3) delta 10.23 (s, 1H), 9.09 (s, 1H), 8.77 (d, J = 2.0 Hz, 1H), 8.72 (s, 1H), 8.10 (d, J = 2.0 Hz, 1H), 7.87 (d, J = 9.0 Hz, 2H), 7.34 (d, J = 8.7 Hz, 2H), 5.47 (d, J = 3.5 Hz, 1H), 4.94 (d, J = 51.5 Hz, 1H), 4.18 (s, 1H), 3.64 (ddd, J = 41.8, 13.5, 3.1 Hz, 1H), 3.43 – 3.38 (m, 1H), 3.02 (d, J = 11.9 Hz, 1H).

24340-77-0, As the paragraph descriping shows that 24340-77-0 is playing an increasingly important role.

Reference£º
Patent; Shenzhen Targetrx, Inc.; WANG, Yihan; ZHAO, Jiuyang; AL, Yixin; (51 pag.)EP3553057; (2019); A1;,
Isothiazole – Wikipedia
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A common heterocyclic compound, the isothiazole compound, name is 3-Chlorobenzo[d]isothiazole,cas is 7716-66-7, mainly used in chemical industry, its synthesis route is as follows.,7716-66-7

Preparation Example 20: 3-(4-(Benzo[d]isothiazoI-3-yl)piperazin-l- yl)propan-l-amine dihydrochloride; A mixture of piperazine (10.2 g, 0.118 mmol) and 3-chloro-l ,2- benzisothiazole (4.0 g, 0.024 mmol) in t-BuOH (4 mL) was refluxed overnight. The reaction mixture was poured into water (100 mL) and extracted with toluene (200 mL). The organic phase was dried over MgSO4 and evaporated until about 20 mL remained, under vacuum. The resulting suspension was cooled at 0-5 0C overnight. The precipitate was filtered and dried under vacuum to provide 3-(piperazin- l-yl)benzo[d]isothiazole as an intermediate (3.36 g, 15.4 mmol, 65 percent). MH+ 220A mixture of 3-(piperazin-l-yl)benzo[-i]isothiazole (1.75 g, 8.0 mmol), N-(3-bromopropyl)-phthalimide (1.96 mmol, 7.3 mmol) and K2CO3 (2.21 g, 16.0 mol) in DMF (10 mL) was stirred at 80 0C for 3 hours. The reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (150 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was further purified by flash column chromatography to provide 2-(3-(4- (benzo[d]isothiazol-3-yl)piperazin-l-yl)propyl)isoindoline-l ,3-dione as an intermediate (1.49 g, 3.67 mmol, 50 percent).To a solution of 2-(3-(4-(benzo[y]isothiazol-3-yl)piperazin-l- yl)propyl)isoindoline- l ,3-dione (1.49 g, 3.67 mmol) in EtOH (25 mL) was added Hydrazine monohydrate (2.5 mL). The mixture was stirred at 80 0C for 1-2 hours and cooled to room temperature. The reaction mixture was poured into water (100 mL) and extracted with DCM (150 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was redissolved in ether (20-30 mL) and HCl solution (3 mL, 2M in ether) was added to the solution. The resulting precipitate was collected on a filter funnel and dried under vacuum to provide the title compound as HCl salt form (1.1 g, 3.15 mmol, 86 percent).1R NMR (400 MHz, CD3OD3) delta 8.04 (d, J = 8.4 Hz, IH), 7.94 (d, J = 8.0 Hz, IH), 7.55 (t, J = 7.2 Hz, IH), 7.45 (t, J = 7.6 Hz, IH), 4.24- 4.14 (br, 2H), 3.85 (t, J = 7.2 Hz, IH), 3.76-3.66 (br, 2H), 3.59-3.32 (m, 9H), 3.08 (t, J = 7.6 Hz, IH), 2.34-2.30 (m, IH), 2.25-2.17 (m, 2H).MH+ 277

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Reference£º
Patent; GREEN CROSS CORPORATION; LEE, Jinhwa; KANG, Suk Youn; PARK, Eun-Jung; SONG, Kwang-Seop; KIM, Min Ju; SEO, Hee Jeong; LEE, Suk Ho; KIM, Jeongmin; PAE, Ae Nim; PARK, Woo-Kyu; WO2010/38948; (2010); A2;,
Isothiazole – Wikipedia
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A common heterocyclic compound, the isothiazole compound, name is 3-Chlorobenzo[d]isothiazole,cas is 7716-66-7, mainly used in chemical industry, its synthesis route is as follows.,7716-66-7

(1) A dry 2-neck 500mL RBF was charged with 21percent sodium ethanolate (46.2 ml, 124 mmol), diluted with 151 mL absolute EtOH, cooled in an ice bath and treated dropwise with diethyl malonate (18 mL, 118 mmol) under an atmosphere of nitrogen. After stirring for 20 minutes, the ice bath was removed and 3-chlorobenzo[d]isothiazole (20.0 g, 118 mmol) was added in one portion and stirred for 24 hours. The reaction solution was quenched with water, extracted with ether and treated with excess 4M HCl/dioxane. The resulting pinkish-white precipitate was filtered off, suspended in water, basified with Na2CO3, extracted with ether, washed with water and brine, dried over sodium sulfate, filtered and concentrated to yellow solids (?20g) which were recrystallized from ethanol/water and dried in a vacuum oven at 60¡ãC for 3 hrs affording 19.9 g (76percent yield) of the ethyl 3-aminobenzo[b]thiophene-2-carboxylate.

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Patent; Universal Display Corporation; Joseph, Scott; Boudreault, Pierre-Luc T.; Dyatkin, Alexey Borisovich; Li, David Zenan; Xia, Chuanjun; Yamamoto, Hitoshi; EP2910555; (2015); A1;,
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