Heterocyclic Building Blocks-Isothiazole

24340-77-0, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,24340-77-0 ,4-Bromoisothiazole, other downstream synthetic routes, hurry up and to see

Name is 4-Bromoisothiazole, as a common heterocyclic compound, it belongs to isothiazole compound, and cas is 24340-77-0, its synthesis route is as follows.

A solution of 5,7-dimethyl-N-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)pyrazolo[l,5-a]pyrimidine-3-carboxamide 6 (286 mg, 0.73 mmol) in DMF (5 mL) was charged with 4-bromoisothiazole (100 mg, 0.60 mmol), potassium acetate (179 mg, 1.8 mmol) and Pd(dppf)Cl2DCM adduct (49 mg, 0.06 mmol) under argon at room temperature. The reaction mixture was heated to 100C for 16 h. The reaction mixture was quenched with water (5 mL), extracted with ethyl acetate (3 X 10 mL) and concentrated under vacuum to obtain crude compound. The crude compound was purified by FCC (eluent, 3-5% methanol in DCM) to afford the title compound as an off-white solid (50 mg, 23%).XH NMR (400 MHz, CDCI3) delta 10.24 (s, 1H), 8.79 (s, 1H), 8.71 (s, 1H), 8.68 (s, 1H), 7.84 (d, J=8.57 Hz, 2H), 7.61 (d, J=8.57 Hz, 2H), 6.78 (s, 1H), 2.83 (s, 3H), 2.74 (s, 3H). ES-MS m/z 350.20 (M+H)+. HPLC purity 99.1%.

Reference£º
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse, Marie Josee; (139 pag.)WO2016/73895; (2016); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

87691-88-1, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,87691-88-1 ,3-Piperazinobenzisothiazole hydrochloride, other downstream synthetic routes, hurry up and to see

Name is 3-Piperazinobenzisothiazole hydrochloride, as a common heterocyclic compound, it belongs to isothiazole compound, and cas is 87691-88-1, its synthesis route is as follows.

To a solution containing 3- (1-piperazinyl) -1,2_ benzisothiazole hydrochloride (100g) and potassium carbonate (136g) in acetonitrile (800ml) added 1,4_ dibromobutane suspension ( 110g). Vigorous stirring mixture was refluxed for 10 hours, the solvent was distilled off pressure acetonitrile was added water (100ml) and toluene (300ml) to the reaction mixture was distilled net was effected under stirring to break up the product mixture, refluxing under stirring operation , the net after the water addition, cooling down, the suspension was filtered to give a white inorganic salts and organic salts of a mixture of the crude quaternary spiro ammonium base (280g).

Reference£º
Patent; Yantai Besten Pharmaceutical Co., Ltd.; Bi, Haidong; Zhang, Yifang; (8 pag.)CN105669665; (2016); A;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

Name is 3-Piperazinobenzisothiazole hydrochloride, as a common heterocyclic compound, it belongs to isothiazole compound, and cas is 87691-88-1, its synthesis route is as follows.

To a flask equipped with mechanical stirrer, thermometer, condenser and nitrogen inlet was added 6-cUoro-5-(2-cHoroethyl)-l,3-dihydro-2H-indol-2- one (9.0 g, 39.1 mrnol), 3-(l-pirhoerazinyl)-l,2-benzoisothiazole hydrochloride (10.0 g, 39.1 mmol), sodium carbonate (9.96 g, 117.5 mmol) and poly(ethylene glycol) methyl ether (Mn= 350, 40 mL) and the suspension was heated to 120- 1250C under nitrogen for about 48 hrs. The suspension was cooled and poured into water. The suspension was cooled to 20-250C, the product was collected by filtration on a Buchner funnel and the filter cake was rinsed with water at 20-250C. The damp product was transferred to a flask equipped with mechanical stirrer, 100 mL of water were added and the suspension stirred at ambient temperature for 1 h. The suspension was filtered, washed with water and transferred to a drying oven and dried in vacuo. This afforded 14.2 g (88% yield) of crude ziprasidone.

Reference£º
Patent; APOTEX PHARMACHEM INC.; WO2006/47893; (2006); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

822-82-2, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,822-82-2 ,Isothiazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see

As a common heterocyclic compound, it belongs to isothiazole compound, name is Isothiazole-4-carboxylic acid, and cas is 822-82-2, its synthesis route is as follows.

A solution of Example 9b (0.19 M in N,N-dimethylacetamide, 237 muL, 0.045 mmol), N,N-diisopropylethylamine (0.21 M in N,N-dimethylacetamide, 262 muL, 0.055 mmol), HATU (0.21 M in N,N-dimethylacetamide, 238 muL, 0.05 mmol), and isothiazole-4-carboxylic acid (0.4M in N,N-dimethylacetamide, 125 muL, 0.05 mmol) were aspirated from their respective source vials, mixed through a perfluoroalkoxy alkanes mixing tube (0.2 mm inner diameter), and loaded into an injection loop. The reaction segment was injected into the flow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mL internal volume) set at 100 C., and passed through the reactor at 180 muL min-1 (10 minute residence time). Upon exiting the reactor, the reaction was loaded directly into an injection loop and purified using preparative HPLC to yield the title compound (9.95 mg, 49.50% yield). Samples were purified by preparative HPLC on a Phenomenex Luna C8 (2) 5 mum 100 AXIA column (50 mm¡Á21.2 mm). A gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 30 mL/min (0-0.5 minutes 5% A, 0.5-6.5 minutes linear gradient 5-60% A, 6.5-7.0 minutes linear gradient 60-100% A, 7.0-8.9 minutes 100% A, 8.9-9.0 minutes linear gradient 100-5% A, 9.0-10 minutes 5% A). A sample volume of 1.0 mL was injected directly from the flow reactor stream to the HPLC system. A custom purification system was used, consisting of the following modules: Gilson 305 and 306 pumps; Gilson 806 Manometric module; Gilson UV/Vis 155 detector; Gilson 506C interface box; Gilson FC204 fraction collector; Agilent G1968D Active Splitter; Thermo MSQ Plus mass spectrometer. The system was controlled through a combination of Thermo Xcalibur 2.0.7 software and a custom application written in-house using Microsoft Visual Basic 6.0. 1H NMR (400 MHz, DMSO-d6) delta 4.69 (d, J=3.9 Hz, 2H), 5.62 (s, 2H), 6.43 (s, 1H), 6.84 (d, J=2.0 Hz, 1H), 7.51 (d, J=2.0 Hz, 1H), 8.18 (s, 1H), 8.32 (s, 1H), 8.96 (s, 1H), 9.59 (s, 1H). MS (APCI) m/z 439.1 [M+H]+.

Reference£º
Patent; AbbVie Inc.; Dai, Yujia; McClellan, William; Michaelides, Mike; Sweis, Ramzi; Wilson, Noel; Dietrich, Justin; (90 pag.)US2017/174688; (2017); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

936-16-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,936-16-3 ,2,3-Dihydrobenzo[d]isothiazole 1,1-dioxide, other downstream synthetic routes, hurry up and to see

Name is 2,3-Dihydrobenzo[d]isothiazole 1,1-dioxide, as a common heterocyclic compound, it belongs to isothiazole compound, and cas is 936-16-3, its synthesis route is as follows.

Ethyl chloroformate (136ml) was added dropwise to a chilled solution of 2,3-dihydro- 1,2-benzisothiazol-1 ,1 -dioxide (68.Og) in pyridine (340ml) over 1h, maintaining the temperature below 180C. The slurry was stirred for 10min at 2O0C, diluted dropwise with water (1000ml) over 75min and stirred for a further 30min. The mixture was chilled to 0-50C, aged for 1 h and isolated by filtration. The cake was washed with cold water (2x250ml), and dried in vacuo to give the title compound as a white solid (72.35g).400 MHz NMR in dimethyl sulphoxide-d6. Dimethyl sulphoxide-d5 as reference at 2.50 ppm. delta (ppm): 1.30 (3) t J=7.1Hz, 4.32 (2H) q J=7.1Hz, 5.01 (2H) s, 7.64-7.70 (2H) m, 7.81 (1 H) td J=7.6Hz J=1.0Hz, 7.98 (1 H) d J=8.0Hz

Reference£º
Patent; GLAXO GROUP LIMITED; WO2006/129100; (2006); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis,18480-53-0,3,4-Dichloroisothiazole-5-carboxylic acid,I believe this compound will play a more active role in future production and life.

18480-53-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3,4-Dichloroisothiazole-5-carboxylic acid, cas is 18480-53-0,the isothiazole compound, it is a common compound, a new synthetic route is introduced below.

3,4-Dichloroisothiazol-5-carboxylic acid (0.235 g, 1.2 mmol), dichloromethane (6 ml), N,N-dimethylformamide (2 drops) were added dropwise to the reaction flask. Add oxalyl chloride (1 g, 8 mmol),The reaction solution was stirred at room temperature for 4 hours.The solvent was then evaporated to give 3,4-dichloroisothiazol-5-carbonyl chloride, which was dissolved in dichloromethane (2 mL).Then 4-fluoro-2-(2-pentyloxy)aniline (0.197 g, 1 mmol) was added to the reaction flask and triethylamine (0.13 mL) was added.Further, a 3,4-dichloroisothiazol-5-formyl chloride solution was added dropwise to the reaction flask, and the mixture was stirred at room temperature for 16 hours.Then after monitoring the reaction by thin layer chromatography,Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate.The organic layer was washed with saturated brine.After drying over anhydrous sodium sulfate, it was concentrated under reduced pressure.The residue was purified by column chromatography (eluent: petroleum ether: ethyl acetate = 20:1).Obtained a fresh yellow solid of 0.236 g.The yield was 62.76percent.

Reference£º
Patent; Shanghai Taihe International Trade Co., Ltd.; Ma Wenjing; Lv Liang; Li Hongwei; Hou Shuang; Du Yonglei; Liu Jiyong; (31 pag.)CN108383791; (2018); A;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis,87691-88-1,3-Piperazinobenzisothiazole hydrochloride,I believe this compound will play a more active role in future production and life.

87691-88-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3-Piperazinobenzisothiazole hydrochloride, cas is 87691-88-1,the isothiazole compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 59; (R)(-)-N-{5-[2-(4-BENZO[D]ISOTHIAZOL-3-YL-PIPERAZIN-1-YL)- ETHYL1-INDAN-2-YLl-ACETAMIDE; A slurry of (R)-N- [5- (2-Chloro-ethyl)-indan-2-yl]-acetamide (2. 00g, 8. 41mmole), Na2CO3(1. 5eq) and 3-Piperazin-1-yl-benzo [d] isothiazole hydrochloride (2. 0eq) in H20 (20moi) was reacted under microwave assistance using a CEM MARS-5 microwave reactor to 175C for 10min. Upon cooling, the reaction was diluted with EtOAc (250moi), H20 (100mol) and the layers separated. The aqueous layer was extracted with EtOAc (2x 50ml). The organics were dried (MgSO4), concentrated, and the residue purified by chromatography (EtOAc) to give (R) (-)-N- {5- [2- (4- Benzo [d] isothiazol-3-yl-piperazin-1-yl)-ethyl]-indan-2-yl}-acetamide (2. 92g, 6. 94mmole) in 100% purity 254 nm; LCMS (APCI) 474 [M+H] +. [a] D25- 3. 6 (c 5.5, CHCl3). 1 H NMR (400 MHz, CHLOROFORM-D) 8 ppm 1.94 (s, 3 H) 2.65-2. 71 (m, 2 H) 2.73-2. 80 (m, 6 H) 2.81-2. 87 (m, 2 H) 3.28 (ddd, J=16. 04,6. 10,5. 92 Hz, 2 H) 3.57-3. 62 (m, 4 H) 4.69-4. 76 (m, 1 H) 5.70 (d, J=7.08 Hz, 1 H) 7.06 (d, J=7.81 Hz, 1 H) 7.11 (s, 1 H) 7.16 (d, J=7.56 Hz, 1 H) 7.35 (ddd, J=8.17, 7.08, 1.10 Hz, 1 H) 7.46 (ddd, J=8.11, 7.02, 1.22 Hz, 1 H) 7.81 (dt, J=8.05, 0.85 Hz, 1 H) 7.91 (dt, J=8.30, 0.98 Hz, 1 H).

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC?; WO2005/56540; (2005); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

It is a common heterocyclic compound, the isothiazole compound, 3-Piperazinobenzisothiazole hydrochloride, cas is 87691-88-1 its synthesis route is as follows.

General procedure: The arylhaloketone (I) (0.1 mol) and the hydrochloride salt of piperazine (pyridinium) compound (II) (0.1 mol) were dissolved in acetonitrile (100 mL) and diisopropylethylamine (0.2 mol) was added.After 12 h at room temperature, TLC (methylene chloride_methanol=20:1) showed that the reaction of starting material (I) was complete.The solvent was concentrated to dryness, and dichloromethane (100 mL) and saturated brine (40 mL) were added and the mixture was stirred for 20 min.The organic layer was dried over anhydrous MgSO4, filtered, concentrated and purified by silica gel column chromatography (eluent:Dichloromethane/methanol = 30:1) gave intermediate (III) in a yield of 60-85% (based on arylhaloketone I).

Reference£º
Patent; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Li Jianqi; Gu Zhengsong; Xie Peng; Zhou Ainan; Xiao Ying; (31 pag.)CN107586281; (2018); A;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3-Piperazinobenzisothiazole hydrochloride, 87691-88-1

3-Piperazin-1-yl-benzoisothiazole hydrochloride (5. 29 G, 20.7 MMOL) and 4, 5-dimethoxy-2-nitrophenylacetic acid (5 g, 20.7 MMOL) were combined in 200 mL methylene chloride with triethylamine (5.77 mL, 41.4 MMOL). This solution stirred for 15 min before BIS- (2-OXO-3-OXAZOLIDINYL) phosphinic chloride (5.26 g, 20.7 MMOL) was added. After stirring overnight at rt, the reaction was quenched with water and extracted into methylene chloride. The organic layer was washed with 0.5 N HCI, water, sodium bicarbonate then water before it was dried over NA2SO4 and concentrated. The residue was taken up in methylene chloride and washed with water. The organic layer was dried over sodium sulfate, and concentrated then purified by MPLC using a Biotage prepacked silica gel cartridge eluting with 3% methanol in methylene chloride to afford 6.5 g of a tan solid. Yield 71% ; 100% purity at 214 nm; LCMS (APCI) : 443 [M+H] + ; MP 170C.

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/41793; (2004); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

7716-66-7, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,7716-66-7 ,3-Chlorobenzo[d]isothiazole, other downstream synthetic routes, hurry up and to see

As a common heterocyclic compound, it belongs to isothiazole compound, name is 3-Chlorobenzo[d]isothiazole, and cas is 7716-66-7, its synthesis route is as follows.

A solution of the product from step b) (200 mg) and 3-chloro-1, 2-benzisothiazole (171mg) in NMP (2ml) and 4M hydogen chloride in dioxan (0.2 ml) was stirred at [140¡ãC] overnight and then at [150 ¡ãC] for 1 hour. and evaporated. The residue was taken up in ethyl acetate, washed with brine (3X), dried [(MGSO4)] and evaporated. The residue was purified by silica chromatography using 20percent acetone in isohexane as eluent to give the title compound (219 mg). MS: APCI (-ve): 331 [[M+H] +] [APOS;H] NMR (DMSO-d6) [8] 8.33 [(1H,] s), 8.01 [(1H,] d), 7.66 [(1H,] d), 7.56 [(1H,] t), 7.39 [(1H,] t), 6.99 [(1H,] d), 2.34 (3H, s), 1.79 (3H, d).

Reference£º
Patent; ASTRAZENECA AB; WO2003/101981; (2003); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com