Day: August 27, 2020

1,2-Thiazinane 1,1-dioxide, cas is 37441-50-2, it is a common heterocyclic compound, the thiazines compound, its synthesis route is as follows.

8-HYDROXY- [1, 6] naphthyridine-7-carboxylic acid methyl ester 1A. 4 (WO 0230930 A2, p. 171) is reacted with one molar equivalent of N-bromosuccinimide in dichloromethane, to yield 5-BROMO-8-HYDROXY- [1, 6] NAPHTLIYRIDINE-7-CARBOXYLIC acid methyl ester, 1A. 5. The phenol is then reacted with p-toluenesulfonyl chloride and triethylamine in CHLOROFONN, FOR example as described in WO 02 30931 A2 p. 72, to give 5-bromo-8- (toluene-4-sulfonyloxy)- [1, 6] naphthyridine-7-carboxylic acid methyl ester 1A. 6. The product is then reacted with [1, 2] thiazinane 1, 1-dioxide 1A. 7 and cuprous oxide in pyridine at reflux, for example as described in WO 0230931 A2, p. 73, to produce 5- (1, 1-DIOXO- 1,2] thiazinan-2-yl)-8- (toluene-4-sulfonyloxy)- [1, 6] naphthyridine-7-carboxylic acid methyl ester 1A. 8. Deprotection, for example by reaction with methanol sodium methoxide in DIMETHYLFORMAMIDE, as described in WO 0230931 A2 p. 74, then affords the phenol 1A. 9.

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Reference£º
Patent; GILEAD SCIENCES, INC.; WO2005/28478; (2005); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

1,2-Thiazinane 1,1-dioxide, cas is 37441-50-2, it is a common heterocyclic compound, the thiazines compound, its synthesis route is as follows.

Intermediate 524-Fluoro- 2-(l,l-dioxo-llambda6-[l,2]thiazinan-2-yl)benzonitrile: To a solution of l,l-dioxo[l,2]thiazinane (8.84 g, 65.4 mmol) in DMF (20 mL) and THF (10 mL) was added portion-wise sodium hydride (1.65 g, 65.5 mmol, 95%). After stirring for 30 min, 2,4-difluorobenzonitrile (10.0 g, 72 mmol) was added and the mixture was stirred at 90 C for 2.5 h. The mixture was cooled and concentrated and the residue was purified by flash chromatography eluting with 0%-l 0% EtOAc/hexane to give the title compound as white needles (1.37 g, 8% yield). 1H-NMR (500 MHz, CDCl3) delta: 7.70 (IH, dd, J= 8.8, 5.8 Hz), 7.30 (IH, dd, J= 8.8, 2.4 Hz), 7.15-7.12 (IH, m), 3.72 (2H, t, J= 5.3 Hz), 3.33 (2H, t, J= 6.1 Hz), 2.40-2.35 (2H, m), 2.05-2.01 (2H, m). LCMS [M+H]+ calcd for C11H12N2FO2S: 255.06; found: 255.19.

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Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/58646; (2007); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

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

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)-

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

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

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]+.

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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

2-Cyano-phenothiazine, cas is 38642-74-9, it is a common heterocyclic compound, the thiazines compound, its synthesis route is as follows.

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%).

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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

3-Bromo-10H-phenothiazine, cas is 3939-23-9, it is a common heterocyclic compound, the thiazines compound, its synthesis route is as follows.

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.

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Reference£º
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Guo Jianhua; (12 pag.)CN106831645; (2017); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

3-Bromo-10H-phenothiazine, cas is 3939-23-9, it is a common heterocyclic compound, the thiazines compound, its synthesis route is as follows.

In a nitrogen-flushed 250 mL round-bottom flask with a magnetic stir bar and septum 3-bromo-10H-phenothiazine (4.95 g, 17.8 mmol) was dissolved in dry THF (50 mL) under nitrogen. The colorless solution was deaerated by a constant stream of nitrogen through a syringe for 10 min and cooled to 0 C (ice bath/water). Potassium tert-butanolate (2.40 g, 21.4 mmol) was added to the reaction mixture under nitrogen and the reaction mixture was allowed to come to room temperature and then stirred for 1 h. To this solution 1-bromo hexane (3.00 mL, 21.4 mmol) was slowly added by syringe and stirring at room temp was continued for 16 h. The solvents were removed in vacuo and the residue was adsorbed onto celiteand purified by chromatography on silica gel (n-hexane) to give 5.83 g (90%) of 3-bromo-10-hexyl-10H-phenothiazine (1a) as a yellow resin, Rf (n-hexane) = 0.43. The NMR spectra were in excellent agreement with the literature. 1H NMR (300 MHz, acetone-d6): delta = 0.84 (t, 3J = 7.1 Hz, 3 H), 1.23-1.33 (m, 4 H), 1.44 (dt, 3J = 7.2 Hz, 3J = 6.8 Hz, 2 H), 1.77 (dt, 3J = 7.5 Hz, 3J = 7.5 Hz, 2 H), 3.92 (t, 3J = 7.0 Hz, 2 H), 6.95 (d, 3J = 8.7 Hz, 2 H), 7.03 (dd, 3J = 8.2 Hz, 4J = 0.9 Hz, 1 H), 7.14 (dd, 3J = 7.6 Hz, 4J = 1.4 Hz, 1 H), 7.21 (ddd, 3J = 8.2 Hz, 3J = 7.3 Hz, 4J = 1.6 Hz, 1 H), 7.27 (d, 4J = 2.2 Hz, 1 H), 7.32 (dd, 3J = 8.6 Hz, 4J = 2.3 Hz, 1 H). -13C NMR (75 MHz, acetone-d6): delta = 14.2 (CH3), 23.2 (CH2), 27.0 (CH2), 27.4 (CH2), 32.1 (CH2), 47.9 (CH2), 114.7 (Cquat), 116.9 (CH), 118.1 (CH), 123.6 (CH), 124.7 (Cquat), 128.1 (Cquat), 128.1 (CH), 128.6 (CH), 130.0 (CH), 130.9 (CH), 145.7 (Cquat), 145.9 (Cquat).

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Reference£º
Article; Urselmann, Dominik; Deilhof, Konstantin; Mayer, Bernhard; Mueller, Thomas J. J.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2055 – 2064;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

3-Bromo-10H-phenothiazine, cas is 3939-23-9, it is a common heterocyclic compound, the thiazines compound, its synthesis route is as follows.

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.

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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

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

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).

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

A common heterocyclic compound, the thiazines compound, name is (S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide,cas is 154127-42-1, mainly used in chemical industry, its synthesis route is as follows.

Step H: 4(R)-ethylamino-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-l,2- thiazine-6-sulfonamide- 1,1 -dioxide (I); 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 50C and ethylamine gas was purged from its 70% aqueous solution (365 ml) below 10C. 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 50C and 6M hydrochloric acid (600 ml) was added. The reaction mixture was stirred for 1 h at 15 to 20C. 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 x 410 ml). The ethyl acetate layer was evaporated to dryness to yield crude Brinzolamide (29g, 66%). Material was recrystallized from ethanol. [Purity: greater than 99.5%, m.p. 125-1270C]

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Reference£º
Patent; USV LIMITED; WO2008/62463; (2008); A2;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem