Month: September 2020

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 ?ralpha^5-4-r(3-oxo-3,4-dihvdro-2H-benzori,41thiazine-6-carbonyl)-aminol- cvclohexanecarboxylic acid methyl ester: 3-Oxo-3,4-dihydro-2H-benzo[l,4]thiazine-6-carboxylic acid (116 mg, 0.50 mmol, 1.0 eq) is added at room temperature to a stirred solution of tralphar¡ã-4-amino-cyclohexanecarboxylic acid methyl ester (80 mg, 0.50 mmol, 1.0 eq) in 7V,N-dimethylformamide (4 mL), followed by 1-hydroxybenzotriazole (74 mg, 0.55 mmol, 1.1 eq), 7V-(3-dimethylaminopropyl)-N’- ethylcarbodiimide hydrochloride (107 mg, 0.56 mmol, 1.15 eq) and N1N- diisopropylethylamine (192 muL, 1.12 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 afford tralphar¡ã-4-[(3-oxo-3,4-dihydro-2H-benzo[l,4]thiazine-6-carbonyl)- amino] -cyclohexanecarboxylic acid methyl ester as an off-white solid (127 mg, 66% yield).MS m/z (+ESI): 349.2 [M+Eta]”

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, 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 stirred solution of phenothiazine or 2-(trifluoromethyl)-10H-phenothiazine (3 mmol) in dichloromethane (20 mL), K2CO3 (5 mmol) and propargyl bromide (5 mmol) were added carefully and the reaction mixture was refluxed for 7 h. After the reaction, the system was concentrated under vacuum, the residue was dissolved in EtOAc (40 mL) and washed by pure water and brine, and dried over anhydrous Na2SO4 and concentrated under vacuum to afford crude products 8a-8b, which were used in the next reaction without further purification.

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
Article; Zhang, Jun-Xia; Guo, Jiao-Mei; Zhang, Ting-Ting; Lin, Hong-Jun; Qi, Nai-Song; Li, Zhen-Guo; Zhou, Ji-Chun; Zhang, Zhen-Zhong; Molecules; vol. 23; 6; (2018);,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, 154127-42-1,(S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide, 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. 154127-42-1

Compound B (50.0 g, 140.7 mmol) was added to 450 mL of acetonitrile, trimethyl orthoacetate (27.0 g, 225.1 mmol) and triethylamine (1.4 g, 14.0 mmol) were added with stirring, and the mixture was heated to 78C. , stirring for 5h,HPLC monitoring showed complete reaction and the HPLC monitoring results are shown in Table 1 (see FIG. 1).Cool to 40C, distill off under reduced pressure, and concentrate to a minimum volume.Compound C crude product was obtained.The crude compound C was dissolved in 180 mL of tetrahydrofuran, cooled to -10 DEG C, triethylamine (31.3 g, 309.5 mmol) was slowly added dropwise at a drip rate of 1 d/s, and the addition was completed at a drip rate of 3 d/s. 4- A solution of tosyl chloride (53.5 g, 280.6 mmol) in 70 mL of tetrahydrofuran. After the addition, the temperature was controlled at -4C, and the reaction was complete after about 3 hours.At a controlled temperature of 10 C. or less, a 70% aqueous solution of ethylamine (361.0 g, 5.6 M) was slowly added dropwise at a rate of 5 d/s. After the addition, the temperature was kept stirring at 12C and the reaction was complete after about 15 hours.The mixture was concentrated under reduced pressure to 70-80 mL, and the temperature was lowered to 0C. The temperature was controlled below 30C, and concentrated hydrochloric acid (12 mol/L) was added dropwise to adjust the pH to 1 to 2, and then about 14 mL of concentrated hydrochloric acid (12 mol/L) was added. The mixture was stirred at room temperature for 1 hour. The reaction was extracted twice with methyl tert-butyl ether (2*250 mL). The organic phases were combined and extracted once with dilute hydrochloric acid (1 mol/L, 100 mL). Combine the aqueous phases, slowly add sodium bicarbonate solids, adjust the pH to 5-6, add 150 mL of water, and adjust the pH to 7-8 with 7% sodium bicarbonate solution. After adjustment, stir at room temperature for 15 h and slowly crystallize. After filtration, the filter cake was rinsed with 30 mL of water and the cake was dried to obtain 35.4 g of product with a purity of 98.3%.Add 250 mL of dichloromethane, 25 mL of methanol to the filter mother liquor, stir, extract, separate, and concentrate the organic phase to dryness4.6 g of yellow viscous material was added and 10 mL of ethyl acetate was added. Heat to 70 ~ 75 C dissolved, slowly dropped to 0 ~ 10 C, stirring 1 ~ 2h, precipitation of a white solid, continue stirring 3 ~ 4h, filtration, with 3mL water filter cake, filter cake drying,Obtained product 2.4g, purity 97.3%.Combined, the purity was 98.1%, the total yield was 65.3%, the ignition residue was 0.08%, and the chiral purity was 99.7%.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,154127-42-1,(S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide,its application will become more common.

Reference£º
Patent; Shandong Weizhi Pharmaceutical Co., Ltd.; Shanghai Weizhi Pharmaceutical Technology Co., Ltd.; Wang Jianhua; He Yigang; Wei Yanjun; Xing Yanping; Zhao Tianchang; (27 pag.)CN107759618; (2018); A;,
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

3-QxQ-3, 4-dihydro-2H-benzo [1, 48thiazine-6-carboxylic acid methyl ester (6.74g) was suspended in tetrahydrofuran (lOOmL) and 2M sodium hydroxide (30mL) was added followed by water (20mL). The solution was stirred for 2.5 hours, evaporated to half volume and acidified with 2M hydrochloric acid. The product was collected, washed with water and dried in vacuo, to give a white solid (6.2g). MS (-ve ion electrospray) m/z 208 (M-H)-

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; SMITHKLINE BEECHAM P.L.C.; WO2003/87098; (2003); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

154127-42-1 A common heterocyclic compound, 154127-42-1,(S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide, 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.

Prepare a 1L three-vial bottle equipped with a mechanical stirrer, a constant pressure dropping funnel, and an ice water bath.Added compound of formula A (50 g, 0.14 mol) and acetonitrile (250 mL),Under N2 protection, stirring and cooling to 5 ~ 10 C,Then DMF-DMA (17.5 g, 0.147 mol) was added dropwise thereto.The rate of addition is such that the stability of the system does not exceed 15C.After the addition, cooling was removed and the reaction was continued for 1 hour. TLC detected the disappearance of the starting material.Concentrate at normal pressure, recover the solvent and add the residue to DCM.Rotary evaporation is replaced by desolvation, and the mixture is finally dried under high vacuum for 1 hour. The residue is the compound of formula B-2.Can be directly after the subsequent reaction without purificationThe crude product B-2 was obtained in equivalent yield.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,154127-42-1,(S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide,its application will become more common.

Reference£º
Patent; Shanghai Bo Shirui Life Technology Co., Ltd.; Wang Dong; Wang Fangdao; Wang Meng; Cai Maojun; (16 pag.)CN107722043; (2018); 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

Compound 13; 10-[3-(N-Boc-4-piperidyl)propyl]-2-trifluoromethylphenothiazine; To a stirred solution of 2-trifluoromethylphenothizine 1 (400 mg, 1.5 mmol), sodium hydride (100 mg, 2 mmol) in DME (10 mL) at 90 C was added N- Boc-4-(3-bromopropyl)piperidine 12 (380 mg, 1.24 mmol) dropwise under an atmosphere of argon. The reaction mixture was stirred for 12h at reflux. The reaction mixture was filtered and the filtrate was concentrated under vacuum. The residue was partitioned between ethyl acetate (25 mL) and brine (1OmL). The organic layer was dried over anhydrous sodium sulphate, filtered, and evaporated. The resulting residue was purified by silica gel column chromatography (8:2 hexane : ethyl acetate) on silica gel to give phenothiazine derivative 13 (425 mg, 70percent) as a solid. MS(ESI): m/z493 (M+H).

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, 98827-44-2,Methyl 4-hydroxy-2H-thieno[2,3-e][1,2]thiazine-3-carboxylate 1,1-dioxide, 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. 98827-44-2

98827-44-2, 260 kg of 4-hydroxy-2H-thieno [2,3-e] -1,2-thiazine-3-carboxylic acid methyl ester 1,1-dioxide were dissolved in500kgDMF, add potassium carbonate 150kg, warmed to 140 C, and dropping 120kg of dimethyl carbonate, 2h drop end, after the dropwise addition, the reaction was continued for 5h, then add 140kg of potassium carbonate, dropping 300 kg of 2 – aminopyridine in dimethylformamide (DMF) (120kg 2-aminopyridine dissolved in 180 kg DMF), 2h addition was complete, the reaction was continued for 5h. After the reaction, cooling and filtering to remove potassium carbonate, the filtrate was recovered under reduced pressure most of the DMF, the residue was added mass concentration of 3% sodium hydroxide alkaline water, activated carbon bleaching, filtration, the filtrate was purified hydrochloric acid to pH = 3 -4, precipitated yellowish solid, centrifuged, the material was washed until neutral, dried, to give a yellow solid 276kg, yield 83%, product purity 99.85%.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98827-44-2,Methyl 4-hydroxy-2H-thieno[2,3-e][1,2]thiazine-3-carboxylate 1,1-dioxide,its application will become more common.

Reference£º
Patent; Jiangsu Engineering Polytechnic College; Yan Bin; Feng Chengliang; Guo Liqiang; (5 pag.)CN106916169; (2017); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.92-30-8,2-(Trifluoromethyl)-10H-phenothiazine,as a common compound, the synthetic route is as follows.,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.

92-30-8 2-(Trifluoromethyl)-10H-phenothiazine 7082, athiazines compound, is more and more widely used in various.

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

Name is 3-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acid, as a common heterocyclic compound, it belongs to thiazines compound, and cas is 272437-84-0, its synthesis route is as follows.,272437-84-0

3-Oxo-3,4-dihydro-2H-benzo[l,4]thiazine-6-carboxylic acid (31 mg, 0.14 mmol, 1.0 eq) is added at room temperature to a stirred solution of l-(6-methoxy-3,4-dihydro-2H-l-oxa-9-aza- phenanthrene-3-yl)-piperidin-4-ylamine (50 mg, 0.14 mmol, 1.0 eq) in N,N- dimethylformamide (3 mL), followed by 1-hydroxybenzotriazole (21 mg, 0.15 mmol, 1.1 eq), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (31 mg, 0.16 mmol, 1.15 eq) and NN-diisopropylethylamine (53 mu, 0.31 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 crude product that is purified by preparative HPLC to afford 3-oxo-3,4- dihydro-2H-benzo[ 1 ,4]thiazine-6-carboxylic acid [ 1 -(6-methoxy-3 ,4-dihydro-2H- 1 -oxa-9- aza-phenanthrene-3-yl)-piperidin-4-yl] -amide as an off-white lyophilizated powder (24 mg, 33% yield). 1H-NMR (400 MHz, DMSO-dtf) delta ppm: 10.66 (br, 1H), 8.33 (s, 1H), 8.24 (d, J = 7.6 Hz, 1H), 7.81 (d, J = 9.0 Hz, 1H), 7.42 (m, 2H), 7.38 (m, 1H), 7.20 (m, 2H), 4.47 (d, J = 11.0 Hz, 1H), 4.02 (m, 1H), 3.93 (s, 3H), 3.78 (m, 1H), 3.50 (s, 2H), 3.20 (m, 1H), 3.08 (m, 2H), 3.00 (m, 2H), 2.42 (m, 2H), 1.81 (m, 2H), 1.58 (m, 2H).MS m/z (+ESI): 505.2 [M+H]+.

With the complex challenges of chemical substances, we look forward to future research findings about 3-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acid

Reference£º
Patent; BASILEA PHARMACEUTICA AG; GAUCHER, Berangere; DANEL, Franck, Hubert; TANG, XiaoHu; XIE, Tong; XU, Lin; WO2011/73378; (2011); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

As a common heterocyclic compound, it belongs to thiazines compound, name is 2-(Trifluoromethyl)-10H-phenothiazine, and cas is 92-30-8, its synthesis route is as follows.,92-30-8

General procedure: To a solution of hydroxy compounds, sulfhydryl compounds oramino compounds (1.0 eq) and propargyl bromide (1.2 eq) inacetone (20 ml) was added NaOH (1.5 eq), the mixturewas refluxedfor about 6 h. Upon completion, the residue was purified withcolumn chromatography (hexane:EtOAc 7:1) to obtain analogue13a~13m. Sulfonyl chlorides (1.0 eq) and propynylamine (1.2 eq) inCH2Cl2 (20 ml) was added Et3N (1.5 eq), the mixture was stirred atroom temperature for about 6 h. Upon completion, the residue waspurified with column chromatography (hexane:EtOAc 9:1) toobtain analogue 13n~13o.

With the complex challenges of chemical substances, we look forward to future research findings about 92-30-8,belong thiazines compound

Reference£º
Article; Fu, Dong-Jun; Li, Ping; Wu, Bo-Wen; Cui, Xin-Xin; Zhao, Cheng-Bin; Zhang, Sai-Yang; European Journal of Medicinal Chemistry; vol. 165; (2019); p. 309 – 322;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem