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 3-oxo-3,4-dihvdro-2H-benzori,41thiazine-6-carboxylic acid (l-[2-(6- methoxy-quinolin-3-ylsulfanyl)-ethyll-piperidin-4-vU -amide: 3-oxo-3,4-dihydro-2H-benzo[l,4]thiazine-6-carboxylic acid (21 mg, 0.09 mmol, 1.0 eq) is added at room temperature to a stirred solution of l-[2-(6-methoxy-quinolin-3-ylsulfanyl)- ethyl]-piperidin-4-ylamine (30 mg, 0.09 mmol, 1.0 eq) in N,N-dimethylformamide (3 mL), followed by 1-hydroxybenzotriazole (13 mg, 0.10 mmol, 1.1 eq), N-Q- dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (20 mg, 0.10 mmol, 1.15 eq) and N,N-diisopropylethylamine (35 muL, 0.20 mmol, 2.25 eq). After 15 hours stirring at room temperature, solvent is evaporated and the residue is extracted with dichloromethane (3 x 5 mL) and water (5 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[l,4]thiazine-6-carboxylic acid {l-[2-(6-methoxy-quinolin-3- ylsulfanyl)-ethyl]-piperidin-4-yl} -amide as a white solid (30 mg, 59% yield).1H-NMR (400 MHz, DMSO-t/6) delta ppm: 11.65 (s, IH), 8.65 (d, J = 2.5 Hz, IH), 8.20-8.25 (m, 2H), 7.88 (d, J = 8.8 Hz, IH), 7.30-7.45 (m, 5H), 3.93 (s, 3H), 3.75 (m, IH), 3.50 (s, 2H), 3.29 (t, J = 7.0 Hz, 2H), 2.95 (m, 2H), 2.66 (t, J = 7.0 Hz, 2H), 2.11 (m, 2H), 1.78 (m, 2H), 1.58 (m, 2H). MS m/z (+ESI): 509.3 [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,3-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acid,272437-84-0,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, 37441-50-2,1,2-Thiazinane 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. 37441-50-2

Part E 7-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1FI imidazo[4,5-c]quinolin-4- amine (0.75 g), 1,4-butanesultam (0.29 g), copper (I) (68 mg), (No.)-trans-1,2- diaminocyclohexane (42 muL), potassium phosphate (0.79 g) and dioxane (4 mL) were added to a scintillation vial. The vial was flushed with nitrogen, sealed with a Teflon- lined cap, placed in an oil bath, and heated at 110 C for 30 hours. The reaction was cooled to ambient temperature, diluted with chloroform and filtered through a bed of CELITE filter agent. The solvent was evaporated and the residue was purified by column chromatography on a Biotage HorizonNo. High-Performance Flash Chromatography instrument using a silica gel cartridge. The polar component of the eluent was chloroform:methanol:ammonium hydroxide 80:18:2 (CMA). The purification was carried out eluting with chloroform: CMA in a gradient from 99: 1 to 90: 10. Additional purification by recrystallization from acetonitrile provided 0.47 g of 7-(1,1-dioxo- [1,2]thiazinan-2-yl)-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H imidazo[4,5-c]quinolin- 4-amine as pale yellow crystals, mp 172-174 C.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,37441-50-2,1,2-Thiazinane 1,1-dioxide,its application will become more common.

Reference£º
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2005/123080; (2005); A2;,
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

In a 250 ml three-necked flask, 0.01 mol of raw material A1, 0.012 mol of raw material B1, 150 ml of toluene were added under a nitrogen atmosphere, and the mixture was stirred and mixed.Then, 0.03 mol of sodium t-butoxide, 5 ¡Á 10 -5 mol of Pd 2 (dba) 3, 5 ¡Á 10 -5 mol of tri-tert-butylphosphine was added, and the mixture was heated to 105 C, and refluxed for 24 hours.The sampling point plate shows that no raw material A1 remains, the reaction is complete; it is naturally cooled to room temperature, filtered, and the filtrate is steamed to a non-fraction (-0.09 MPa, 85 C) under reduced pressure, and passed through a neutral silica gel column to obtain an intermediate B1.HPLC purity 99.2%, yield 75.2%;

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; Jiangsu March Optoelectric Technology Co., Ltd.; Tang Dandan; Zhang Zhaochao; Li Chong; Zhang Xiaoqing; (44 pag.)CN108218853; (2018); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, 37441-50-2,1,2-Thiazinane 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. 37441-50-2

A flask was charged under nitrogen with 1,1-dimethylethyl 3-bromo-5-iodobenzoate (D7)(1 g, 2.6 mmol, 1 equiv), Cs2CO3 (1.26 g, 3.9 mmol, 1.5 equiv),tris(dibenzylideneacetone)dipalladium(0) (12 mg, 0.013 mmol, 0.005 equiv), Xantphos (22 mg, 0.038 mmol, 0.015 equiv) and toluene (20 ml). Tetrahydro-2H-1,2-thiazine 1,1-dioxide (D6) (350 mg, 2.9 mmol, 1.1 equiv) was then added and the resulting mixturewas stirred at 100C for 16 h then cooled to room temperature and diluted with AcOEt.The organic phase was washed with saturated aqueous NaHCO3 solution, dried overMgSO4 and concentrated in vacua. The residue was triturated with Et2O to give 1,1-dimethylethyl 3-bromo-5-(1,1-dioxidotetrahydro-2/-/-1,2-thiazin-2-yl)benzoate (D8) (590mg, 58%) as a white solid.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,37441-50-2,1,2-Thiazinane 1,1-dioxide,its application will become more common.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2004/111022; (2004); 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

Tri-tert-butylphosphine (4.4 mL of a 1.0 M solution in toluene, 1.48 g, 0.05 mmol), palladium acetate (0.4 g,1.83 mmol) and sodium tert-butoxide (52.7 g, 549 mmol) were added to 2-6-a (20.423 g, 73.42 mmol) and 2-6-c(11.53 g, 73.42 mmol) a solution in degassed toluene (500 mL), and the mixture was warmed under reflux for 2 hr.The reaction mixture was cooled to room temperature, diluted with toluene and filtered over EtOAc. Dilute the filtrate with water and use aThe benzene was extracted and the organic phases were combined and evaporated under vacuum. The residue was passed through silica gel (heptane / dichloromethane)Filtration was carried out and crystallized from isopropanol. Obtaining 2-6-b 19.51 g, yield 75%; the resulting bromide 2-6-b(7.89 g, 20 mmol), pinacol borate (6.22 g, 24 mmol), 1,1′-bis(diphenylphosphino)-ferrocene-palladium dichloride(II) dichloromethane complex (0.49 g, 0.6 mmol), potassium acetate (5.90 g, 60 mmol) and 79 ml of toluene were reacted under refluxAfter 16 hours, cool, add 26 ml of water and stir for 30 minutes.The organic phase is separated and filtered through a short bed of diatomaceous earth, followed by organicThe solvent was distilled off and the crude product was recrystallized from heptane / toluene.The compound 2-6 was obtained in an amount of 6.58 g, yield 82%.

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.; Zhang Hong; Cai Hui; (36 pag.)CN108530418; (2018); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A common heterocyclic compound, 38642-74-9,2-Cyano-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. 38642-74-9

General procedure: In an air atmosphere, 2-phenylindole 1a (0.60 mmol), phenothiazine 2a (0.30 mmol),10mol% cuprous bromide and DMF (2mL) were added to the Schlenk reaction tube in sequence.In a constant temperature heating magnetic stirrer, the reaction was stirred at room temperature for 24 hours.After the reaction was completed, it was quenched with distilled water, extracted with ethyl acetate (3 ¡Á 20 mL), and the organic layers were combined.After drying over anhydrous sodium sulfate and spinning the organic phase, The crude product by column chromatography to give the pure product 3a (103.1 mg, 88%)., 38642-74-9

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,38642-74-9,2-Cyano-phenothiazine,its application will become more common.

Reference£º
Patent; Henan Normal University; Zhao Peizheng; Wang Ke; Liu Jianming; Wang Zhixian; Shao Huibin; Yue Yuanyuan; (9 pag.)CN110407830; (2019); A;,
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

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]+.

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; TANG, XiaoHu; XIE, Tong; XU, Lin; WO2011/73378; (2011); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

92-39-7 A common heterocyclic compound, 92-39-7,2-Chloro-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.

(1) Dehydration reaction: 2-chlorophenothiazine, cuprous cyanide, catalyst, quinoline, p-toluenesulfonyl chloride according to moleThe ratio is 1:1.25:0.15:5:0.1 is added to the reactor, and the temperature is raised to 120 C for dehydration reaction, the reaction is 1 hour, and the water is dehydrated to a moisture content of less than 0.1%;The catalyst is a mixture of sodium iodide and lithium iodide, and the molar ratio of sodium iodide to lithium iodide is 1:0.3;(2) Preparation of crude 2-cyanophenothiazine: the temperature of the reactor was raised to 230 C, and the reaction was carried out for 15 hours;(3) Separation of crude 2-cyanophenothiazine: the reactor temperature was lowered to 90 C, and 8 times was added to the reactor.The total amount of moles of the starting material is water, the solid is precipitated and filtered, and the product is extracted with ethyl acetate and concentrated to dryness to give a crude 2-cyanophenothiazine;(4) Purification of 2-cyanophenothiazine: a crude 2-cyanophenothiazine is placed in a mixed solvent of toluene and methanol,The volume ratio of toluene to methanol in the mixed solvent was 1:0.15, the temperature was raised to 120 C for 30 minutes, and the mixture was cooled to 20 C, and the precipitated solid was filtered to obtain 2-cyanophenothiazine.After testing, the yield of 2-cyanophenothiazine prepared in this example was 92.6%, and the purity of the product was 99.61%.The content of the amide was 0.03%.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,92-39-7,2-Chloro-10H-phenothiazine,its application will become more common.

Reference£º
Patent; Ningbo Jinuo Chemicals Co., Ltd.; Peng Zhigang; Yue Mingxin; Qu Qiangzheng; (8 pag.)CN105175355; (2018); B;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

38642-74-9 A common heterocyclic compound, 38642-74-9,2-Cyano-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.

General procedure: In an air atmosphere, 2-phenylindole 1a (0.60 mmol), phenothiazine 2a (0.30 mmol),10mol% cuprous bromide and DMF (2mL) were added to the Schlenk reaction tube in sequence.In a constant temperature heating magnetic stirrer, the reaction was stirred at room temperature for 24 hours.After the reaction was completed, it was quenched with distilled water, extracted with ethyl acetate (3 ¡Á 20 mL), and the organic layers were combined.After drying over anhydrous sodium sulfate and spinning the organic phase, The crude product by column chromatography to give the pure product 3a (103.1 mg, 88%).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2-Cyano-phenothiazine,38642-74-9,its application will become more common.

Reference£º
Patent; Henan Normal University; Zhao Peizheng; Wang Ke; Liu Jianming; Wang Zhixian; Shao Huibin; Yue Yuanyuan; (9 pag.)CN110407830; (2019); A;,
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

Step J: (+)-4-Ethylamino-3,4-dihydro-2-(3-methoxy)propyl-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide hydrochloride To a solution of the product from Step I (2.4 g, 6.74 mmol) and triethylamine (3.8 mL, 27 mmol) in anhydrous tetrahydrofuran (20 mL) cooled to -20 C. was added tosyl chloride (2.6 g, 13.5 mmol); this mixture was allowed to warm to room temperature and stirred for 18 hr. The reaction mixture was cooled to -60 C. and ethylamine (10 mL) was added and the mixture was again allowed to warm to room temperature. After 18 hr the reaction mixture was diluted with ethyl acetate (200 mL), washed with a saturated aqueous solution of sodium bicarbonate (3*50 mL), dried (MgSO4), and evaporated to give the crude product which was purified by column chromatography [silica; CH3 OH/CH2 Cl2 (20:1)] to give 1.3 g (52%) of the desired amine. The free base was dissolved in ethanol (5 mL) and treated with a 2M solution of hydrochloric acid in ethanol (4 mL) at room temperature. Evaporation of the solvent provided a solid which was recrystallized from methanol: methylene chloride to give 950 mg (34%) of the desired product; mp 175-177 C.; [~]D +10.35 (C=1.00, H2 O). Analysis. Calculated for C12 H22 ClN3 O5 S3: C, 34.32; H, 5.28; N, 10.00 Found: C, 34.26; H, 5.23; N, 9.92., 154127-42-1

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; Alcon Laboratories, Inc.; US5378703; (1995); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem