Day: September 4, 2020

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-Oxo-3, 4-dihydro-2H-benzo [1, 4] thiazine-6-carboxylic acid methyl ester (6.74 g) was suspended in tetrahydrofuran (100 ml) and 2M sodium hydroxide [(30] ml) was added followed by water (20 ml). 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 (6.2 g). MS (-ve ion electrospray) [L} L/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,Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate,188614-01-9,its application will become more common.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2004/2992; (2004); 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]+.

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

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 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, 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

Acid (4a) in tetrahydrofuran (SOmL) and triethylamine (4.7mL) was cooled to 0C and isobutylchloroformate (4.02mL) was added dropwise and the solution was stirred at 0C for 2 hours, when it was filtered into a stirred solution of sodium borohydride (3. 14g) in ice/water (50mL). The mixture was stirred at 0C for 1 hour and allowed to warm to room temperature. It was acidified with 2M hydrochloric acid, evaporated to half volume, and the resulting product was collected, washed with water and dried in vacuo, to give a white solid (4. 5g). MS (-ve ion electrospray) m/z 194 (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; SMITHKLINE BEECHAM P.L.C.; WO2003/87098; (2003); 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: 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,92-30-8,2-(Trifluoromethyl)-10H-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, 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

After dissolving 2-(trifluoromethyl)-10H-phenothiazine (2.0 g, 7.48 mmol) in N,N-dimethylformamide (2 mL), 60% sodium hydride (149.70 mg, 3.74 mmol) and 1-bromo-4-chlorobutane (1.16 mL, 10.10 mmol) were added at 0 C. The reactants were heated at 100 C. for 12 hours under reflux. After the reaction was completed, the reaction solution was extracted with ethyl acetate and the organic layer was dried with magnesium sulfate, filtered under reduced pressure and then concentrated under reduced pressure. The target compound (1.52 g) was obtained with a yield of 56.72% by separating the residue by chromatography (ethyl acetate/n-hexane=1/20). 1H NMR (400 MHz, CDCl3): delta 1.89-2.00 (4H, m, 2CH2), 3.40 (1H, t, J=6.02 Hz, CH), 3.54 (1H, t, 6.18 Hz, CH), 3.94 (2H, t, 6.02 Hz, CH2), 6.89 (1H, d, J=8.12 Hz, CH), 6.96 (1H, t, 7.44 Hz, CH) 7.03 (1H, s, CH), 7.13-7.17 (2H, m, 2CH), 7.21 (2H, t, 8.16 Hz, 2CH).

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; Korea Institute of Science and Technology; Roh, Eun Joo; Jeon, Bo Ra Mi; Lee, Chang Joon; Hong, Jin Pyo; Jeong, Joo Yeon; Kang, Sang Soo; (28 pag.)US10035795; (2018); B1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

3080-99-7 A common heterocyclic compound, 3080-99-7,3,4-Dihydro-2H-benzo[b][1,4]thiazine, 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.

(3d) Potassium carbonate (5.2 g, 37.7 mmol) and methyl 4-(bromomethyl)benzoate (2.8 g, 12.6 mmol) were added to a solution of (3c) (1.9 g, 12.6 mmol) in 20 mL of anhydrous DMF. The reaction mixture was heated to 80 C. overnight. After cooling to rt, the solid was filtered off and rinsed with DMF. The filtrate was concentrated in vacuo and the residue was purified on silica gel column to provide methyl 4-(2,3-dihydro-4H-1,4-benzothiazin-4-ylmethyl)benzoate (3.02 g, 80%).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3080-99-7,3,4-Dihydro-2H-benzo[b][1,4]thiazine,its application will become more common.

Reference£º
Patent; Duan, Jingwu; Jiang, Bin; Chen, Lihua; Lu, Zhonghui; Barbosa, Joseph; Pitts, William J.; US2003/229084; (2003); A1;,
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 (VII) (112g, 0.313 mol) was suspended in tetrahydrofuran (10 vol). Methanesulfonic anhydride (65.7g, 0.374 moles) was added in one lot and stirred. The reaction mixture was cooled to 0-50C and pyridine (2.5 vol) was added slowly over a period of 45 minutes. The reaction was monitored by TLC [Mobile phase dichloromethane: methanol, 9.5:0.5] for completion. As reaction product the intermediate compound (Vila) was obtained.To the above reaction mixture 70% aqueous ethylamine solution (400 ml, 10 vol) was added slowly at 0-5C. After the complete addition, the reaction mixture was stirred at 25-300C for 12.0 h. The reaction is monitored by TLC [Mobile phase dichloromethane: methanol, 9.5:0.5] for completion. The organic layer (ethylamine and tetrahydrofuran mixture) was distilled off completely below 500C under reduced pressure. The aqueous phase was acidified with concentrated hydrochloric acid and the pH adjusted to 3.0 at 15-25C. The aqueous phase was extracted with t-butyl methyl ether twice (2 x 2.0 vol) to remove any organic impurities if present. The t-butyl methyl ether layer was extracted with 1 N HCI solution and the layers separated.The aqueous layers were combined, treated with activated charcoal and heated at 65-700C. The contents were stirred at 65-700C for 30 minutes, filtered through hyflo supercel at 65-700C and washed with preheated water(65-700C). The filtrate was cooled to 25-30C and the pH was adjusted to 8 with solid sodium bicarbonate. The reaction mixture was stirred for 12 h for crystallization. If the crystallization did not occur, the reaction mass was filtered through a Bchner funnel, extracted with ethyl acetate (3 x 5.0 vol), dried over sodium sulphate and filtered. The organic layer was distilled completely (below 500C) under reduced pressure. The crude product was obtained as a pale yellow syrup, which was washed with hexane (4 x 1.0 vol) to yield a residue which crystallized to a solid on standing.Yield of crude compound (VIIl): 8Og (66.3%)

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; AZAD PHARMACEUTICAL INGREDIENTS AG; RAMAKRISHNAN, Arul; SONI, Anil Kumar; ADHIKARI, Sujit Das; RAO, Kommula Srinivasa; PAUL, Soumendu; SRINIVASULU, Ganta; WO2010/103115; (2010); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

3080-99-7 A common heterocyclic compound, 3080-99-7,3,4-Dihydro-2H-benzo[b][1,4]thiazine, 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.

Example 9: Synthesis of 2- (2, 3-DIHYDROBENZOLL, 4] thiazin-4-ylmethyl)-1, 1, 1-TRIFLUORO-4- (5- fluoro-2-methoxyphenyl)-4-methylpentan-2-ol A solution of 2- [2- (5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (118 mg) and 3, 4-dihydro-2H-1, 4-benzothiazine (H. I. EL-SUBBAGH et AL., Arch. Pharm. Med. Chem., 1999, 332, pp. 19-24) (122 mg) in dimethylformamide (1 mL) was heated at 140C for 73 hours. The resulting mixture was diluted with diethyl ether, washed with saturated aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by radial chromatography with a chromatotron (eluted with 0% to 1% ethyl acetate-hexanes) to give the title compound as a white solid (53.5 mg), m. p. 103C-104C.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3080-99-7,3,4-Dihydro-2H-benzo[b][1,4]thiazine,its application will become more common.

Reference£º
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2004/63163; (2004); 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

Step2 A strong glass tube was charged with Pd2(dba)3 (6.4 mg; 0.007 mmol), xantphos (12 mg; 0.02 mmol), 1,2-thiazinane-1,1-dioxide (115 mg; 0.85 mmol), and Cs2CO3 (323 mg; 0.99 mmol).The tube was capped with a rubber septum, evacuated and backfilled with nitrogen. 6-Bromo-1-methyl-1H-indole carboxylic acid ethyl ester (200 mg; 0.71 mmol) in 1 ml of 1,4-dioxane was added through the septum.The septum was replaced with a Teflon screwcap.The tube was sealed, and the mixture was stirred at 100 C. for 64 hours.The reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 ml), filtered, and concentrated in vacuo.The crude material was purified by flash chromatography (silica gel, ethyl acetate-hexane 1:1) to afford 190 mg (66%; m/z 337) of colorless crystals.This compound was dissolved in a mixture of tetrahydrofuran (4 ml), methanol (2 ml) and water (1 ml).To this solution was added dropwise LiOH monohydrate (95 mg; 2.26 mmol) dissolved in 1 ml water and the mixture was stirred at room temperature for 16 h.The reaction mixture was partition between ethyl acetate and water.The aqueous layer was acidified with 2N HCl to ph ~3-4 and extracted with ethyl acetate.The organic layer was washed with brine and dried (Na2SO4) and evaporated in vacuo.Yield 131 mg of 6-(1,1-Dioxo-1lambda6-[1,2]thiazinan-2-yl)-1-methyl-1H-indole-2-carboxylic acid as a white powder (75%); m/z 307.

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; Bamberg, Joe Timothy; Gabriel, Tobias; Krauss, Nancy Elisabeth; Mirzadegan, Taraneh; Palmer, Wylie Solang; Smith, David Bernard; US2004/77646; (2004); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem