September 2020 | Page 9 of 23 | Heterocyclic Building Blocks-Thiazines

A new synthetic route of (S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide

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.

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

To a solution of IX (41 g, 0.12 moles) and triethylamine (33 ml. 0.24 moles) in anhydrous tetrahydrofuran (615 ml) cooled to 0 to 5 C. was added a solution of tosyl chloride (44 g, 0.24 moles) in tetrahydrofuran (205 ml). The mixture was allowed to warm to room temperature and stirred for 18 hours. The reaction mixture was cooled to 0 to 5 C. and ethylamine gas was purged from its 70% aqueous solution (365 ml) below 10 C. Reaction mixture was allowed to attain ambient temperature and stirred for 36 hours. The reaction mixture was concentrated and ethyl acetate (615 ml) was added to it. Further the organic layer was washed with water (410 ml). The concentrated ethyl acetate layer and MDC (615 ml) was added followed by cooling to temperature 0 to 5 C. and 6M hydrochloric acid (600 ml) was added. The reaction mixture was stirred for 1 h at 15 to 20 C. Aqueous layer was washed with MDC (205 ml). pH of the aqueous solution was adjusted to 8 using sodium bicarbonate solution causing white solid to precipitate which was extracted with ethyl acetate (2*410 ml). The ethyl acetate layer was evaporated to dryness to yield crude Brinzolamide (29 g, 66%). Material was recrystallized from ethanol. [Purity: greater than 99.5%, m.p. 125-127 C.], 154127-42-1

Reference£º
Patent; Sathe, Dhananjay Govind; Tarur, Radhakrishnan Venkatasubramanian; Bhise, Nandu Baban; Shinde, Ajit Bhaskar; Pardeshi, Santosh; US2010/9977; (2010); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

Some scientific research about 3-Bromo-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,3-Bromo-10H-phenothiazine,3939-23-9,its application will become more common.

3939-23-9 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.

2, under the protection of nitrogen will be prepared in step 1 aromatic diamine 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.

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 new synthetic route of 2-Methoxyphenothiazine

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1771-18-2,2-Methoxyphenothiazine,its application will become more common.

A common heterocyclic compound, 1771-18-2,2-Methoxyphenothiazine, 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. 1771-18-2

Step a 4-(3′-indolyl)-1-[1″-(2′”-methoxy-10′”-phenothiazinyl) -2″-methyl-3″-propionyl]-piperidine hydrochloride A mixture of 23 g of 2methoxy-phenothiazine, 21 g of methacryloyl chloride and 120 ml of toluene was refluxed for 3 hours and was then cooled and washed with 250 ml of N sodium hydroxide. The organic phase was decanted and the aqueous phase was washed twice with 50 ml of toluene. The combined organic phases were washed with water, dried over magnesium sulfate, treated with carbon black and evaporated to dryness to obtain 29.6 g of 2-methoxy-10-(alpha-methyl acryloyl)-phenothiazine melting at 91-92 C.

Reference£º
Patent; Roussel-UCLAF; US3988453; (1976); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A new synthetic route of 92-30-8

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.

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

A mixture of 1-1 [2-(trifluoromethyl)-l0i7-phenothiazine] (300 mg, 1.12 mmol), 1- bromo-4-chlorobutane (391 mg, 2.28 mmol) and CS2CO3 (1.04 g, 3.19 mmol) in DMF (15 mL) was stirred at rt overnight. The mixture was poured into cool water (20 mL) and extracted with EtOAc (15 mL x 3). The combined organic extracts were washed with brine, dried over NaiSCE. fdtered and concentrated under reduced pressure. The residue was purified by column chromatography (petrol ether: EtOAc =10: 1) to provide a yellow solid (240 mg, 60% yield). LC-MS: Rt = 2.30 min; ESI, m/r 358 [M + 1] +

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

The origin of a common compound about 2-(Trifluoromethyl)-10H-phenothiazine

General procedure: Phenothiazine 1 (5g, 25.09mmol) was taken in anhydrous N, N-dimethyl formamide (DMF) (50mL) in a dry round bottom flask. Sodium hydride (2g, 50.18mmol) was added under nitrogen condition at 0C and stirred for 30min at room temperature. Methyl iodide (3.4mL, 50.18mmol) was added and continued the stirring for 8h. After that, the reaction mixture (monitored by TLC) was quenched with ice cold water (150mL). The separated solid was filtered off, dried and used as such for the next step.

Reference£º
Article; Reddyrajula, Rajkumar; Dalimba, Udayakumar; Madan Kumar; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 263 – 282;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

Some scientific research about 3939-23-9

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

Step 2, 132 mmol of 9-BBN was dissolved in THF at 0 C, 44 mmol of 1-2, Stirring for 15min, warming to 35 degrees Celsius, reaction 3h, and then transferred to the mixture containing 5-1 66mmoltetrakis(triphenylphosphine)palladium 0.88 mmol, sodium carbonate 132 mmol in toluene: ethanol: water = 4: 1: 1, and the temperature was raised to reflux temperature reaction24h. The crude product was passed through a silica gel column to give the product 20 mmol, 5-2.

Reference£º
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Sun Keyi; Cai Hui; (31 pag.)CN106946934; (2017); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

Some scientific research about 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,3-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acid,272437-84-0,its application will become more common.

272437-84-0 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.

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)-

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

Some scientific research about 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.

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]+.

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

The origin of a common compound about 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.

To a stirred solution of 3-bromo-1OH-phenothiazine(1 8 g, 64.72 mmol) in DIVIF (100 mL) was added sodium hydride (3.8 g, 97.08 mmol) at 0 C in small portions and the reaction mixture was stirred at 0 C for 15 mins. To the reaction mixture was added 3-bromo chloropropane (12.2 g,77.66 mmol) at 0 C and stirring continued at room temperature for 1 h. The reaction wasquenched with aq.NH4C1 solution, extracted with EtOAc, organic layer is washed with brine, dried over anhydrous sodiumsulphate, and concentrated. The crude product (20 g) was as such taken for the next step without further purification: MS (ESI) m/z3 55 (M+2H).

Reference£º
Patent; BIOIMICS AB; KIRSEBOM, Leif; UPADHAYAYA, Ram Shankar; KETHIRI, Raghava Reddy; VIRTANEN, Anders; (308 pag.)WO2017/222466; (2017); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

The important role of 92-30-8

With the complex challenges of chemical substances, we look forward to future research findings about 2-(Trifluoromethyl)-10H-phenothiazine

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

With the complex challenges of chemical substances, we look forward to future research findings about 2-(Trifluoromethyl)-10H-phenothiazine