September 2020 | Page 3 of 23 | Heterocyclic Building Blocks-Thiazines

Some scientific research about 37441-50-2

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

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., 37441-50-2

Reference£º
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2005/123080; (2005); A2;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A new synthetic route of 3-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acid

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.

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-dihydro-2H-benzo[l,41thiazine-6-carboxylic acid [tra/? -4-(8- methoxy-l,2-dihydro-3-oxa-5,9-diaza-cyclopenta[alnaphthalen-2-ylmethyl)-cyclohexyll- amide: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 tra?s-4-(8-methoxy-l,2-dihydro-3-oxa-5,9- diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine (47 mg, 0.14 mmol, 1.0 eq) in N,N-dimethylformamide (4 mL), followed by 1-hydroxybenzotriazole (24 mg, 0.16 mmol, 1.1 eq), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (32 mg, 0.16 mmol, 1.15 eq) and NN-diisopropylethylamine (56 mu, 0.32 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[l,4]thiazine-6-carboxylic acid [tra?s-4-(8-methoxy-l,2-dihydro-3-oxa- – -5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-amide as a white lyophilized powder (16 mg, 21% yield).1H-NMR (400 MHz, DMSO- 6) delta ppm: 10.67 (s, 1H), 8.49 (s, 1H), 8.23 (d, J = 7.9 Hz, 1H), 8.19 (d, J = 9.0 Hz, 1H), 7.44 (m, 3H), 7.06 (d, J = 9.1 Hz, 1H), 5.21 (m, 1H), 4.01 (s, 3H), 3.74 (m, 2H), 3.51 (s, 2H), 3.14 (dd, J = 7.9, 16.8 Hz, 1H), 1.80-2.00 (m, 5H), 1.66 (m, 1H), 1.57 (m, 1H), 1.39 (m, 2H), 1.13 (m, 2H).MS m/z (+ESI): 505.5 [M+H]+.

Reference£º
Patent; BASILEA PHARMACEUTICA AG; GAUCHER, Berangere; DANEL, Franck Hubert; XIE, Tong; XU, Lin; WO2012/171860; (2012); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

Some scientific research about 2-(Trifluoromethyl)-10H-phenothiazine

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.

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.

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.

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

A new synthetic route of 37441-50-2

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.

(39) A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 1-6 (56 mg, 0.10 mmol), 1,4-butanesultam (52 mg, 0.38 mmol), 8-hydroxyquinoline (6 mg, 0.040 mmol) and K2CO3 (50 mg, 0.36 mmol) in DMSO (1 mL) was degassed before being charged with CuI (10 mg, 0.052 mmol). The mixture in a sealed tube was heated at 130 C. overnight. The mixture was then purified by HPLC to give the titled compound (10 mg). MS 451.1 and 453.1 (M+H, Cl pattern)., 37441-50-2

Reference£º
Patent; Millennium Pharmaceuticals, Inc.; US2007/259924; (2007); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

Some scientific research about 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.

To a solution of 3-oxo-3, 4-dihydro-2H-1, 4-benzothiazin-6- carboxylic acid (3.6 g, 17 mmol) in DMF (50 ML) were added WSC (3.8 g, 20 mmol), HOBt (3.1 g, 20 mmol) and 2.0 M dimethylamine-THF solution (12.5 ML, 25 mmol), and the mixture was stirred at room temperature for 12 hrs. Saturated aqueous sodium hydrogen carbonate was poured into the reaction solution and the mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and saturated brine, dried (MGS04) and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to give the title compound as pale yellow crystals (3.6 g, yield 90%). OH NMR (300 MHz, DMSO-D6) 8 ppm: 2.91 (br, 6 H), 3.49 (s, 2 H), 6. 96-7. 00 (m, 2 H), 7. 35 (d, J = 8. 4 Hz, 1 H).

Reference£º
Patent; TAKEDA CHEMICAL INDUSTRIES, LTD.; WO2004/46107; (2004); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

Some scientific research about Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate

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.

188614-01-9 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.

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)., 188614-01-9

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 new synthetic route of 3-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acid

Preparation of 4-[(3-oxo-3,4-dihydro-2H-benzo[l ,41thiazine-6-carbonyl)-aminol-piperidine- 1-carboxylic acid tert-butyl ester:3-Oxo-3,4-dihydro-2H-benzo[l,4]thiazine-6-carboxylic acid (556 mg, 2.45 mmol, 1.0 eq) is added at room temperature to a stirred solution of 4-amino-piperidine- 1-carboxylic acid tert- butyl ester (500 mg, 2.45 mmol, 1.0 eq) in N,N-dimethylformamide (20 mL), followed by 1- hydroxybenzotriazole (421 mg, 2.69 mmol, 1.1 eq), N-(3-dimethylaminopropyl)-N’- ethylcarbodiimide hydrochloride (550 mg, 2.81 mmol, 1.15 eq) and N,N- diisopropylethylamine (962 L, 5.50 mmol, 2.25 eq). After 15 hours stirring at room temperature, solvent is evaporated and the residue is extracted with dichloromethane (3 x 30 – – mL) and water (30 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: cyclohexane:ethyl acetate :methanol, 1 :3:0 to 0/9/1, v/v/v) to afford 4-[(3-oxo-3,4- dihydro-2H-benzo [ 1 ,4]thiazine-6-carbonyl)-amino ] -piperidine- 1 -carboxylic acid tert-butyl ester as a light yellow solid (621 mg, 62% yield).1H-NMR (400 MHz, DMSO- 6) delta ppm: 10.66 (s, 1H), 8.27 (d, J = 7.8 Hz, 1H), 7.42 (m, 3H), 3.96 (m, 3H), 3.51 (s, 2H), 2.90 (m, 2H), 1.76 (m, 2H), 1.40 (m, 11H).MS m/z (+ESI): 392.3 [M+H]+, 414.3 [M+Na]+.

The origin of a common compound about 188614-01-9

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).

Some scientific research about 2-(Trifluoromethyl)-10H-phenothiazine

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.

A new synthetic route of 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., 37441-50-2

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