Day: September 27, 2020

A common heterocyclic compound, 92-30-8,2-(Trifluoromethyl)-10H-phenothiazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 92-30-8

1 -Bromo-3-chloropropane (37.68 g, 200 mmol) was added to 2-(trifluoromethyl)- l0i7-phenothiazine (26.7 g, 100 mmol) and Cs2CC>3 (65.6 g, 200 mmol) in DMF (130 mL). The mixture was stirred at 30 C for 48 h and then heated to 80 C for 2 h. The mixture was cooled to rt then H20 was added. The mixture was extracted with PE three times (200 mL x 3). The combined organic phase was washed with brine, dried over Na2S04, and concentrated in vacuo. The residue was purified by column chromatography (PE 100%, PE:EtOAc = 60: 1) to get 10.8 g pure and 19 g crude. LC-MS: Rt = 2.29 min; ESI, m/z 344 [M+l]+.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2-(Trifluoromethyl)-10H-phenothiazine,92-30-8,its application will become more common.

Reference£º
Patent; CAMP4 THERAPEUTICS CORPORATION; BUMCROT, David, A.; SEHGAL, Alfica; HERTZOG, Donald L.; (172 pag.)WO2019/195789; (2019); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, 188614-01-9,Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 188614-01-9

A. (3,4-Dihydro-2H-benzo[1,4]thiazin-6-yl)-methanol. To a solution of 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid methyl ester (750 mg, 3.4 mmol) in Et2O (32 mL) was added LiAlH4 (240 mg, 6.3 mmol) and the resulting suspension was stirred at RT for 24 h. The reaction mixture was cooled to 0 C. and treated with H2O (0.5 mL), 15% aq. NaOH (0.5 mL), and H2O (1.5 mL). The resulting suspension was filtered. The filtrate was concentrated to provide 340 mg (58%) of the title compound as an amber oil. MS (ESI): exact mass calculated for C9H11NOS, 181.06; m/z found, 182.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 6.96 (d, J=7.9, 1H), 6.60 (dd, J=7.9, 1.6, 1H), 6.49 (d, J=7.9, 1H), 4.52 (s, 2H), 3.65-3.62 (m, 2H), 3.06-3.04 (m, 2H).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,188614-01-9,Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate,its application will become more common.

Reference£º
Patent; Allison, Brett D.; Gomez, Laurent; Grice, Cheryl A.; Hack, Michael D.; Morrow, Brian J.; Motley, S. Timothy; Santillan, Alejandro; Shaw, Karen J.; Schwarz, Kimberly L.; Tang, Liu Y.; Venkatesan, Hariharan; Wiener, John J. M.; US2006/223810; (2006); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, 92-30-8,2-(Trifluoromethyl)-10H-phenothiazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 92-30-8

To a mixture of 2-(trifluoromethyl)-l0i7-phenothiazine (5.0 g, 18.726 mmol) and NaH (0.674 g, 28.09 mmol) in DMF (50 mL) was added 2-(bromomethyl)oxirane (3.8 g, 28.09 mmol) at 0 C. The mixture was allowed to slowly warm to rt and was stirred at room temperature overnight. Then the mixture was added to water (100 mL) and extracted with EtOAc (100 mL x 3). The combined organic layers were washed with brine (30 mL), dried over sodium sulfate, and concentrated to dryness. The residue was purified by column chromatography on silica gel (PE/EtOAc = 8/1) to afford compound 2-1 (4.5 g, 75% yield) as a white solid. ‘H NMR (400 MHz, Patent; CAMP4 THERAPEUTICS CORPORATION; BUMCROT, David, A.; SEHGAL, Alfica; HERTZOG, Donald L.; (172 pag.)WO2019/195789; (2019); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

92-30-8 A common heterocyclic compound, 92-30-8,2-(Trifluoromethyl)-10H-phenothiazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Compound 2; 10-(3-Chloropropyl)-2-trifluoromethylphenothiazine; To a stirred solution of 2-trifluoromethyl phenothiazine (compound 1) (2g, 7.49 mmol) and sodium hydride (0.5 g, 10.42 mmol) in dry toluene (30 mL) was added l-bromo-3-chloropropane (1.57g, 10 mmol). The reaction mixture was stirred for 18 hours at 110 C under an atmosphere of argon. The solution was cooled to room temperature and poured into an ice- water mixture, the crude product was extracted with ethyl acetate (3×50 mL) and the combined organic phase dried over anhydrous sodium sulphate. Final purification was performed by column chromatography (9:1 hexane: ethyl acetate) on silica gel to give 10-(3- chloropropyl)- 2-trifluoromethylphenothiazine (1.5 g, 58% ) as a solid.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2-(Trifluoromethyl)-10H-phenothiazine,92-30-8,its application will become more common.

Reference£º
Patent; IMMUNE CONTROL, INC.; WO2008/27521; (2008); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, 3939-23-9,3-Bromo-10H-phenothiazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 3939-23-9

Compound 1 was synthesized by the modification of the published method [18]. Sodium hydride(2.2 g, 53.9 mmol) was stirred with 3-bromo-10H-phenothiazine (10.0 g, 35.9 mmol, dissolved in dryDMF) for 30 min. Bromoethane (4.7 g, 43.1 mmol) was then added to the mixture and stirred for 10 hat room temperature in dark environment. After the reaction completed, water was added to react theremaining sodium hydride. White solid was precipitated and collected by vacuum filtration. The solidwas first washed with small amount of EA and then washed with n-hexane. 1H NMR (400 MHz,acetone-d6) 7.34 (dd, J = 8.7, 2.3 Hz, 1H), 7.28 (d, J = 2.3 Hz, 1H), 7.25-7.19 (m, 1H), 7.15 (dd, J = 7.6,1.5 Hz, 1H), 7.04 (dd, J = 8.3, 1.2 Hz, 1H), 6.99 (d, J = 1.2 Hz, 0H), 6.97 (s, 1H), 6.95 (s, 1H), 3.99 (q,J = 6.9 Hz, 2H), 1.38 (t, J = 6.9 Hz, 3H)., 3939-23-9

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3939-23-9,3-Bromo-10H-phenothiazine,its application will become more common.

Reference£º
Article; Lao, Hio Kuan; Tan, Jingyun; Wang, Chunfei; Zhang, Xuanjun; Molecules; vol. 24; 19; (2019);,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, 92-30-8,2-(Trifluoromethyl)-10H-phenothiazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 92-30-8

II-4 (20g, 75mmol) a 100mL reaction flask was added DMF (60mL) was stirred and dissolved, was added potassium carbonate (15.5g, 113mmol), stirred at 60¡ãC , portionwise Intermediate III-5 (17.5g , 79mmol), the reaction after 1h, TLC analysis showed completion of the reaction (developing solvent, ethyl acetate: petroleum ether = 1: 3). The reaction solution was poured into 200ml cold water, with stirring, solid precipitated out.Filter cake was washed with water, and dried to give brown crude solid.The crude product was recrystallized from ethanol to give slightly yellow solid 30.0g. Purity 98.8percent (HPLC normalization method), a yield of 88.3percent.ESI-MS ([M + H] +): 453.0.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,92-30-8,2-(Trifluoromethyl)-10H-phenothiazine,its application will become more common.

Reference£º
Patent; Tianjin Pharmaceutical Institute Co., Ltd.; Liu Ying; Liu Dengke; Mu Shuai; Yue Nan; Gong Min; Zhi Shuang; Liu Changxiao; (25 pag.)CN104230848; (2017); B;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, 188614-01-9,Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 188614-01-9

A. 3-Oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid. To a solution of 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid methyl ester (1.5 g, 6,7 mmol) in a THF/H2O mixture (1:1, 63 mL) was added 4 N LiOH (8.0 mL, 32 mmol) and the resulting solution was stirred at RT for 24 h. The solution was partially concentrated and diluted with H2O (50 mL). The solution was acidified using concentrated HCl and a solid precipitated. The solid was collected via filtration, washed with H2O and dried in vacuo to provide 0.79 g (60%) of the title compound as a white solid. MS (ESI): exact mass calculated for C9H7NO3S, 209.01; m/z found, 210.2 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.65-7.61 (m, 2H), 7.40 (d, J=8.1, 1H), 3.48 (s, 2H).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,188614-01-9,Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate,its application will become more common.

Reference£º
Patent; Allison, Brett D.; Gomez, Laurent; Grice, Cheryl A.; Hack, Michael D.; Morrow, Brian J.; Motley, S. Timothy; Santillan, Alejandro; Shaw, Karen J.; Schwarz, Kimberly L.; Tang, Liu Y.; Venkatesan, Hariharan; Wiener, John J. M.; US2006/223810; (2006); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, 272437-84-0,3-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acid, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 272437-84-0

Preparation of 3-oxo-3,4-dihvdro-2H-benzori,41thiazine-6-carboxylic acid (l-[2-(7- methoxy-quinoxalin-2-yloxy)-ethvH-piperidin-4-vU -amide: 3-Oxo-3,4-dihydro-2H-benzo[l,4]thiazine-6-carboxylic acid (60 mg, 0.26 mmol, 1.0 eq) is added at room temperature to a stirred solution of l-[2-(7-methoxy-quinoxalin-2-yloxy)- ethyl]-piperidin-4-ylamine (80 mg, 0.26 mmol, 1.0 eq) in N,N-dimethylformamide (5 mL), followed by 1-hydroxybenzotriazole (38 mg, 0.29 mmol, 1.1 eq), N-Q- dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (57 mg, 0.30 mmol, 1.15 eq) and N,N-diisopropylethylamine (100 muL, 0.58 mmol, 2.25 eq). After 15 hours stirring at room temperature, solvent is evaporated and the residue is extracted with dichloromethane (3 x 10 mL) and water (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by preparative EtaPLC to afford 3-oxo-3,4- dihydro-2H-benzo[ 1 ,4]thiazine-6-carboxylic acid { 1 -[2-(7-methoxy-quinoxalin-2-yloxy)- ethyl]-piperidin-4-yl} -amide as an off-white solid (18 mg, 13% yield).1H-NMR (400 MHz, DMSO-t/6) delta ppm: 10.65 (s, IH), 8.42 (s,lH), 8.22 (d, J = 7.8 Hz, IH), 7.89 (d, J = 9.0 Hz, IH), 7.38-7.46 (m, 3H), 7.22-7.28 (m, 2H), 4.56 (t, J = 5.8 Hz, 2H), 3.92 (s, 3H), 3.75 (m, IH), 3.50 (s, 2H), 3.00 (m, 2H), 2.81 (t, J = 5.8 Hz, 2H), 2.18 (m, 2H), 1.79 (m, 2H), 1.55 (m, 2H).MS m/z (+ESI): 494.4 [M+H]+., 272437-84-0

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,272437-84-0,3-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acid,its application will become more common.

Reference£º
Patent; BASILEA PHARMACEUTICA AG; GAUCHER, Berangere; DANEL, Franck Hubert; ROUSSEL, Patrick; WO2010/84152; (2010); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, 3939-23-9,3-Bromo-10H-phenothiazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 3939-23-9

2, under nitrogen protection will be prepared in step 1 p-phenylenediamine and phenothiazine derivatives according to 1:1 molar ratio was added to toluene, while adding potassium tert-butyl alcohol and palladium acetate as a catalyst,The reaction was heated to 80 C for 3 hours and then cooled to room temperature. The reaction was filtered,The filtrate was washed with dichloromethane and then the solvent was evaporated to dryness. The crude product was repeatedly washed with methanol and acetone,The product is obtained after purification by column chromatography.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3939-23-9,3-Bromo-10H-phenothiazine,its application will become more common.

Reference£º
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Guo Jianhua; (12 pag.)CN106831645; (2017); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, 92-30-8,2-(Trifluoromethyl)-10H-phenothiazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 92-30-8

General procedure: To a mixture of sodium hydride suspension (60percent, 0.26 g, 6.67 mmol) and phenothiazine derivative in abs. THF (50 cm3) was added the appropriate 3-aryltetrazolo[1,5-a]pyridin-4-ium tetrafluoroborate (1) in portions over 20 min, and the mixture was stirred at room temperature for 2 days. After evaporation of the reaction mixture, the residue was dissolved in a 1:1 mixture of EtOAc:water (50 cm3) and the solid product was filtered off. The aqueous mother liquor was extracted with EtOAc (thrice) and the organic phase was dried over anhydrous Na2SO4, filtered and evaporated. The combined organic solvent was evaporated, the residue was washed with diethyl ether then it was recrystallized from ethyl acetate – unless otherwise stated – to give the product.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2-(Trifluoromethyl)-10H-phenothiazine,92-30-8,its application will become more common.

Reference£º
Article; Taka?cs, Daniella; Nagy, Ildiko?; Bombicz, Petra; Egyed, Orsolya; Jemnitz, Katalin; Riedl, Zsuzsanna; Molna?r, Jo?zsef; Amaral, Leonard; Hajo?s, Gyo?rgy; Bioorganic and Medicinal Chemistry; vol. 20; 14; (2012); p. 4258 – 4270;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem