Tag: M.W:200-300

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

A heterogeneous mix of 6-(chloromethylcarbonyl)-4,4,8-trimethyl-3,4-dihydro-1H-quinolin-2-one (2.200g, 8.739mmole, 1.0eq), sodium carbonate (1.158g, 10.924mmole, 1.25 eq), sodium iodide (0.131 g, 0.874mmole, cat.), and added 3-piperazin-1-yl-benzo[d]isothiazole hydrochloride (3.353g, 13.110mmole, 1.5eq) in acetonitrile (35ml) was heated to 150C under microwave assistance for 30min. The reaction was diluted with H2O (100ml), CH2CI2 (100ml) and the layers separated. The aqueous layer was extracted with CH2Cl2 (2x, 50ml) and the organic layer dried over magnesium sulfate (MgSO4), concentrated, and the residue purified by MPLC (25 % EA/CH2CI2 – 50 % EA gradient over 20min and hold for 20min – 100 % EA gradient over 20min). The title compound was obtained as a white crystalline solid in 63 % yield with 30 % recovered starting material (6-(2-chloro-ethyl)-4,4,8-trimethyl-3,4-dihydro-1H-quinolin-2-one). 1H NMR (400 MHz, CDCl3) delta 7.90 (d, 1H, J = 7.94 Hz), 7.80 (d, 1H, J = 7.94 Hz), 7.46 (t, 1H, J = 7.94 Hz), 7.34 (t, 1H, J = 7.94 Hz), 7.02 (s, 1H), 6.91 (s, 1H), 4.78 (s, 1H), 3.69-3.55 (m, 4H), 2.86-2.59 (m, 8H), 2.45 (s, 2H), 2.21 (s, 3H), 1.30 (s, 6H)

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

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

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

The above intermediate IV (0.01 mol) and the hydrochloride salt of the piperazine compound (V) (0.01 mol) were dissolved in DMF (100 mL), and K2CO3 (0.02 mol) was added.According to the general operation three,Preparation of 3-(3-(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)propyl)-1H-indole-5-hydroxy(VI-10) hydrochloride 3.21g, yield 75%

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

Reference£º
Patent; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Li Jianqi; Gu Zhengsong; Zhou Ainan; Xiao Ying; (26 pag.)CN109467554; (2019); A;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

107869-45-4, 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. (3aR,6S)-8,8-Dimethyl-4,5,6,7-tetrahydro-3H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide, cas is 107869-45-4,the isothiazole compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 1; (1R)-(+)-2,10-Camphor Sultam (Scheme 3, 3-1); To a solution of (-) camphor sulfonic acid (1.45 kg, 6.25 mol) in chloroform (7 L) under reflux condition is added thionyl chloride (0.896 kg, 7.5 mol) over a period of 1 h. The reaction mixture is refluxed for 16 h and then cooled to 4 C. using an ice bath. This cooled reaction mixture is added slowly to conc. NH4OH (15 L) while maintaining the temperature below 15 C. during the addition. After addition, the mixture is stirred for 4 h at room temperature. The organic layer is separated and the aqueous layer is extracted with chloroform (2¡Á2 L). The combined organic extracts are washed with brine (4 L) and dried over MgSO4. After filtration, the filtrate is concentrated under vacuum and dried to give 1.2 kg (83%) of camphor sulfonamide. In one experiment at 145 g scale of camphor sulfonic acid, the use of dichloromethane instead of chloroform for the reaction and extraction gives comparable yields. To a suspension of the camphor sulfonamide (1.2 kg, 5.2 mol) in toluene (15 L) is added Amberlyst H+ resin (150 g), and the mixture is heated at reflux for 4 h with the water formed removed azeotropically using a Dean-Stark water separator. The reaction mixture is filtered hot to remove the resin. The filtrate on cooling gave a white solid which is collected by filtration to give 1.02 kg (92%) of the desired imine. To the above imine (100 g, 0.47 mol) in ethanol (0.75 L) is added Raney Nickel (100 g) and the mixture is hydrogenated at 40 psi for 2 h. The catalyst is removed by filtration and the filtrate concentrated under vacuum to give the product 3-1 as a white solid

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 (3aR,6S)-8,8-Dimethyl-4,5,6,7-tetrahydro-3H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide, 107869-45-4

Reference£º
Patent; BioCryst Pharmaceuticals, Inc.; US2006/128789; (2006); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

94594-90-8, 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. (3aS,6S,7aS)-8,8-Dimethylhexahydro-1H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide, cas is 94594-90-8,the isothiazole compound, it is a common compound, a new synthetic route is introduced below.

Example 3Step 1. Synthesis of (3aS,6R,7aR)-1 -methaciotayloyl-8,8-dimethylhexahydro-3a,6-methano-2,1- benzisothiazole 2,2-dioxide.(1 S)-(-)-2,10-camphorsultamProcedure: To a solution of the (1S)-(-)-2,10-camphorsultam (5.00Og, 23.22 mmoles) in anhydrous THF (50ml) at -20¡ã C was added lithium chloride (1.08g, 25.5 mmoles, – small balls), triethylamine (4.21 ml, 30.2 mmoles, 1.30 equivalents.) and then the mixture was allowed to stir for 10 minutes. The lithium chloride did not go into solution. 2-methylacrylic anhydride (4.15 ml, 27.9 mmoles, 1.20 equivalents.) in THF (15ml) was then added. The internal temperature varied between -20¡ã C and -10¡ã C during addition which took about 5 minutes. The thick white mixture was stirred within the cooling bath and allowed to reach room temperature. After stirring overnight the white heterogeneous reaction mixture was added to 350ml of water with stirring. The white crystalline solid (3aS,6R,7aR)-1 -methacryloyl-8,8- dimethylhexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide (6.302g, 96percent yield) was collected and dried under vacuum.-Analytical HPLC run with a Vydac 218TP54 C18 reverse phase column run with solvents A: 0.1percent trifluoroacetic acid in H2O and B: 0.1percent trifluoroacetic acid in acetonitrile. Gradient (0 to 100percentB) over 22 minutes. Retention time 18.166 min (100percent).Optical rotation = 0.02Og in 2ml; c=0.01g/ml (C= 1 (CHCI3)}; measurement -0.226; optical rotation = – 0.226×4000/10 = – 90.4.Combustion Anal sis:Steps 2 through 5 were performed as in Example 2.

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 (3aS,6S,7aS)-8,8-Dimethylhexahydro-1H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide, 94594-90-8

Reference£º
Patent; PFIZER PRODUCTS INC.; WO2008/65503; (2008); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

As a common heterocyclic compound, it belong isothiazole compound,6-Bromobenzo[d]isothiazole-3-carboxylic acid,677304-75-5,Molecular formula: C8H4BrNO2S,mainly used in chemical industry, its synthesis route is as follows.,677304-75-5

Preparation 45; 6-(4-Hvdroxy-2-methyl-phenyl)-benzordlisothiazole-3-carboxylic acid; To a degassed solution of 6-Bromo-benzo[d]isothiazole-3-carboxylic acid (0.42g, 1.54mmol), 3-Methyl-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl-phenol (0.54, 2.3 lmmol), 2-Dicyclohexylphosphino-2′,6′-dimethoxy- 1 , 1 ‘-biphenyl (0.064g, 0.154mmol), and potassium phosphate (0.7 Ig, 3. lmmol) in dioxane (8mL) and water (4mL) is added Pd(OAc)2 (6.5mg, 0.03mmol). The reaction is degassed again and heated to 80 degrees for 18 h. The reaction is cooled to room temperature and concentrated under reduced pressure. The material is diluted with EtOAc and IN HCl. The layers are separated and concentrated under reduced pressure. The crude material is diluted with 20 mL of MeOH and 2 mL H2SO4 and heated to reflux for 2 h. The reaction is concentrated onto silica and purified using a gradient of 20 to 50% EtOAc in Hexanes to yield the title compound (0.12g, 26% yield). ES/MS m/e 300.0 (M+l).

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Bromobenzo[d]isothiazole-3-carboxylic acid,belong isothiazole compound

Reference£º
Patent; ELI LILLY AND COMPANY; WO2007/140174; (2007); A2;,
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.,87691-88-1

To a flask equipped with mechanical stirrer, thermometer, condenser and nitrogen inlet was added 6-chloro-5-(2-chloroethyl)-l,3-dihydro-2H-indol-2- one (21.6 g, 94 mmol), 3-(l-piperazinyl)-l,2-benzoisothiazole hydrochloride (24 g, 94 mmol), sodium carbonate (29.9 g, 282 mmol) and l-methyl-2- pyrrolidinone (NMP) (96 ml) and the mixture was heated to 130-1350C under nitrogen for about 24 hrs. The mixture was cooled to 40-450C and poured into water. The suspension was cooled and the product was collected by filtration on a Buchner funnel, the filter cake was rinsed with water at 20- 250C and the damp product was transferred to a drying oven and dried in vacuo. This afforded 34.2 g (88.2% yield) of crude ziprasidone. The IR (KBr) and NMR spectra were consistent with those of reference ziprasidone.

With the complex challenges of chemical substances, we look forward to future research findings about 3-Piperazinobenzisothiazole hydrochloride

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

As a common heterocyclic compound, it belong isothiazole compound,3-Piperazinobenzisothiazole hydrochloride,87691-88-1,Molecular formula: C11H14ClN3S,mainly used in chemical industry, its synthesis route is as follows.,87691-88-1

88.7 g (0.837 mols, 3.21 molar equivalents) of sodium carbonate, 600 mL of acetonitrile and 66.7 g (0.261 mols, 1.0 molar equivalent) of 3- (1-piperazinyl) -1, 2- benzisothiazole hydrochloride are added into a beaker equipped with a magnetic stirrer. The resulting white suspension is stirred for 10 minutes. At this point 60.0 g (0.261 mols, 1.0 molar equivalent) of 5- (2- chloroethyl) -6-chloro-l, 3-dihydro-indole-2- (2H) -one and 0.3 g (0.002 mols, 0.008 molar equivalents) of NaI are added. The resulting brown suspension is charged into a 1 L reactor vessel, which is purged with nitrogen and heated to 120-125 C (internal pressure increases to 400- 500 kPa) for 25 hours. The reaction is cooled to room temperature, stirred for 30 minutes, filtered and the solid washed with acetonitrile. A wet mixture of zipradisone and inorganic salts is obtained, that is further washed with acetonitrile. The resulting wet mixture of ziprasidone and inorganic salts is stirred with 675 ml of water at reflux temperature for 1 h to remove inorganic salts. The suspension is cooled to room temperature, stirred for 30 minutes and filtered. The solid is washed with water, and 140 g of wet solid (corresponding to 87 g of dry material) are obtained. EPO The wet solid is stirred again with water at reflux temperature for 1 h to remove residual inorganic salts. The suspension is cooled to room temperature, stirred for 30 minutes and filtered. The solid is washed with water, and 170 g of wet solid (corresponding to 81 g of dry- material) are obtained. HPLC analysis reveals a purity of 97.8%.To remove starting materials present in the wet solid obtained in the previous step, it is stirred twice with400 ml of tetrahydrofuran at reflux temperature. The solution is cooled to room temperature, stirred for 30 minutes and filtered. The solid is washed twice with 40 ml of tetrahydrofuran, and 60 g of wet solid, corresponding to 54.8 g of dry material, are obtained.The solid obtained is ziprasidone base having a purity of 99.4% by HPLC and the global yield from the starting compounds is 51% (molar yield) . Potentiometric titration with HClO4: 100.03%

With the synthetic route has been constantly updated, we look forward to future research findings about 3-Piperazinobenzisothiazole hydrochloride,belong isothiazole compound

Reference£º
Patent; MEDICHEM, S.A.; WO2006/34965; (2006); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

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

EXAMPLE 96; 1-f7-r2- (4-Benzordlisothiazol-3-vl-piperazin-1-yl)-ethvll-3, 4-dihvdro-1 H- isoauinolin-2-vl-2. 2, 2-trifluoro-ethanone methane sulfonate; A mixture of 3-piperazin-1-yl-benzo [d] isothiazole hydrochloride (0.4056 g, 1.417 mmol), 1- [7- (2-chloro-ethyl)-3, 4-dihydro-1 H-isoquinolin-2-yl]-2, 2, 2-trifluoro- ethanone (0.3755 g, 1.287 mmol), anhydrous sodium carbonate (0.3019 g, 2. 848 mmol) and potassium iodide (0.0259 g, 0.156 mmol) in acetonitrile (10 mL) was allowed to react at 175 C for 0.5 h in a microwave reactor. The reaction was cooled to ambient temperature. CH2CI2 and H20 were added and the solution was mixed well then poured into a phase separator. The organic layer was concentrated in vacuo to give an oil. The oil was eluted through a flash column (silica gel 60, 230- 400 mesh, 30-100% EtOAc in CH2CI2 gradient over 1 h) to give a white waxy/gummy solid. Yield : 0.4106 g (0.865 mmol, 67 %). The solid (0.405 g, 0.853 mmol) was taken up in THF (8.5 mL) and heated to 40 C. Methanesulfonic acid (55. 5 J. L, 0.855 mmol) was added and after 5 min, the reaction was allowed to cool to ambient temperature. The product was allowed to crystallize overnight. Hexanes were added to the reaction mixture and the solid was filtered and washed with hexanes. The wet solid was dried in a vacuum oven at 50 C to give a white/off-white crystalline solid as the mesylate salt. Anal. calculated for C24H25F3N40SsCH403S : C, 52.62 ; H, 5.12 ; N, 9.82. Found: C, 52.36, H, 4.98 ; N, 9. 69.’H NMR (400 MHz, CDCI3) 8 11.66 (s, 1 H), 7.84 (d, J=7. 42 Hz, 2 H), 7.52 (m, 2 H), 7.41 (m, 1 H), 7.12 (m, 2 H), 4.76 (m, 4 H), 4.17 (m, 2 H), 4.00 (m, 4 H), 3.82 (m, 2 H), 3.27 (m, 3 H), 2.91 (m, 6 H).

87691-88-1 is used more and more widely, we look forward to future research findings about 3-Piperazinobenzisothiazole hydrochloride

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/66165; (2005); A1;,
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.,87691-88-1

EXAMPLE 75; 5-[2-(4-BENZO[D]ISOTHIAZOL-3-YL-PIPERAZIN-1-YL)-ACETYL]- 1, 1, 3, 3-TETRAMETHYL-INDAN-2-ONE A mixture of 5- (2-Chloro-acetyl)-1, 1,3, 3-tetramethyl-indan-2-one (7.85 g, 29.6 mmol), 3-piperazin-1-yl-benzo[d]isothiazole hydrochloride (7.95 g, 31.1 mmol), potassium carbonate (13.5 g, 97.7 mmol), sodium iodide (4.50 g, 30.0 mmol) in acetonitrile (550 mL) was stirred at rt for 24 h. The reaction was quenched with water (120 mL), and acetonitrile was evaporated. The residue was extracted with methylene chloride (2 x 250 mL). The combined organic extracts were washed with water, brine, dried over Na2SO4, evaporated, and purified by chromatography (silica gel, 7: 3 to 6: 4 hexanes/ethyl acetate) to give 5-[2-(4-Benzo [agisothiazol-3-yl- piperazin-1-yl)-acetyl]-1, 1,3, 3-tetramethyl-indan-2-one (11.2 g, 85%) as an off-white solid :’H NMR (300 MHz, CDC13) 8 8.02 (dd, J= 8.0, 1.6 Hz, 1 H), 7.96 (s, 1 H), 7.91 (d, J = 8.0 Hz, 1 H), 7.83 (d, J = 8.0 Hz, 1 H), 7.47 (t, J = 7.0 Hz, 1 H), 7.38-7. 34 (m, 2H), 3.94 (br s, 2H), 3.67-3. 65 (m, 4H), 2.90- 2.88 (m, 4H), 1.38 (s, 6H), 1.37 (s, 6H).

With the complex challenges of chemical substances, we look forward to future research findings about 3-Piperazinobenzisothiazole hydrochloride

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC?; WO2005/56540; (2005); A1;,
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.,87691-88-1

E. ‘6-r2- (4-Benzordlisothiazol-3-vl-piperazin-1-vl)-ethvl-3, 4-dihvdro-2H- quinolin-1-vlT-(4-fluorophenvl)-methanone (97); A stirred mixture of the product of Step D (2.00 g, 6.29 mmol), 3-piperazin-1- yl-benzo [agisothiazole hydrochloride (9,1. 82 g, 7.12 mmol), K2CO3 (2.34 g, 16.9 mmol), and Nal (1.00 g, 6.67 mmol) in anhyd CH3CN (60 mL) under N2 was heated to reflux for 3 d, then allowed to cool. The mixture was diluted with EtOAc (300 mL), then washed twice with H20 (300 mL), once with saturated NaCI (100 mL), dried over Na2SO4, filtered, and the solvent was removed in vacuo. The residue was purified by column chromatography (silica gel (150 g), 40-60% EtOAc/hexanes containing 1% Et3N) to give the title compound (2.75 g, 87%) as a sticky oil and solid mixture. The product was dissolved in warm EtOAc (60 mL), then allowed to cool with stirring. A small amount of precipitate was observed after 30 min. The mixture was diluted with hexanes (120 mL) portionwise over 2 h. After stirring an additional hour, the precipitate was collected by suction filtration washing with hexanes, then dried in vacuo at 46 C for 3 d to give the title compound (1.71 g, 54%) as a white amorphous solid: mp 126-129 C ; 1H NMR (300 MHz, CDCl3) 8 7.91 (d, J= 8.1 Hz, 1 H), 7.82 (d, J= 8.1 Hz, 1 H), 7.47 (td, J= 7.6, 1.0 Hz, 1 H), 7.32-7. 41 (m, 3 H), 7.02 (br s, 1 H), 6.91-7. 00 (m, 2 H), 6.76 (dd, J = 8. 2,1. 5 Hz, 1 H), 6.60 (brd, J= 7.7 Hz, 1 H), 3.89 (t, J= 6.5 Hz, 2 H), 3.54-3. 63 (m, 4 H), 2.60-2. 87 (m, 10 H), 2.05 (p, J = 6.6 Hz, 2 H) ; IR (ATR) 2947,2835, 1634,1600, 1504,1374, 1271, 1227 cm-1 ; ESI MS m/z501 [C29H29FN40S + H]+; HPLC >99% (AUC), tR = 14.77 min. Anal. calcd. for C29H29FN40S : C, 69.57 ; H, 5.84 ; N, 11.19. Found: C, 69.36 ; H, 5.86 ; N, 11.03.

With the complex challenges of chemical substances, we look forward to future research findings about 3-Piperazinobenzisothiazole hydrochloride

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/66165; (2005); A1;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com