Application of 6-Fluoro-1,2,3,4-tetrahydroquinoline

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 39093-93-1, and friends who are interested can also refer to it.

39093-93-1, A common heterocyclic compound, 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., 39093-93-1

A mixture of (S) – 4 – (1 – (4-fluoro-phenyl) – 2-methoxy-ethylamine) – 5-methyl-pyrrolo [2,1-f] [1, 2, 4] triazine-6-carboxylic acid (100 mg, 0 . 29mmol) and thiomorpholine -1,1-dioxide (58 mg, 0 . 44mmol) dissolved in N, N-dimethyl formamide (5 ml) in, then add 1-hydroxy benzotriazole (51 mg, 0 . 38mmol), 1-ethyl-3 – (3-dimethylamino-propyl) carbodiimide hydrochloride (74 mg, 0 . 38mmol) and triethylamine (88 mg, 0 . 87mmol), stirring the mixture at room temperature until the TLC reaction monitoring raw material the reaction is complete, to be added in to the reaction solution (100 ml), ethyl acetate (50 ml ¡Á 3) extraction, then by saturated sodium chloride solution (100 ml ¡Á 2) washing, the organic phase is dried with anhydrous sodium sulfate, concentrated under reduced pressure, the resulting residue is purified with silica gel column chromatography, to obtain (S) – (1,1-dioxy thiophosphoro morphline) – {4 – [1 – (4-fluorophenyl) – 2-methoxy-ethylamine] – 5-methyl-pyrrolo [2,1-f] [1, 2, 4] triazin-6-yl}}-methyl ketone (105 mg, white solid), yield: 78.4percent., 39093-93-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 39093-93-1, and friends who are interested can also refer to it.

Reference£º
Patent; SHANGHAI CDYMAX PHARMACEUTICALS CO LTD; An, XiaoXia; Bie, PingYan; Yang, wuli; Liu, Jun; (49 pag.)CN103848833; (2016); B;,
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Analyzing the synthesis route of Thiomorpholine 1,1-dioxide

According to the analysis of related databases, 39093-93-1, the application of this compound in the production field has become more and more popular.

39093-93-1, A common heterocyclic compound, 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., 39093-93-1

The above acteyl chloride (1.122 g; 3.27 mmol) was dissolved in 10 mL DMF. Thiomorpholine 1,1-dioxide (0.442 g; 3.27 mmol) was added followed by DIPEA (0.63 mL; 3.6 mol) and DMAP (16 mg; 0.131 mmol). The reaction mixture was heated in a 60¡ã C. oil bath overnight. Water was added to the reaction mixture, and it was extracted with EtOAc three times. The organics were combined and washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The yellow residue obtained was purified by flash column chromatography on silica gel using 2.5percent methanol in DCM mixture as eluent then switched to 5percent methanol in DCM. The title compound was obtained in >95percent purity (HPLC) as a white foam (781 mg; 54percent yield).

According to the analysis of related databases, 39093-93-1, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/9964; (2010); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

Brief introduction of 128453-98-5

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 128453-98-5. We look forward to the emergence of more reaction modes in the future.

4-(tert-Butoxycarbonyl)thiomorpholine-3-carboxylic acid, A common heterocyclic compound, 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., 128453-98-5

Boc protected thiomorpholine carboxylic acid (3.1g, 13mmol), HOBt (2.1g, 16mmol) and EDCI hydrochloride (3.7g, 20mmol) dissolved in DMF(20ml) was added 28% of ammonium hydroxide solution (4.5g, 130mmol) at RT. After 4h, the reaction mixture was poured into saturated water solution of NaHCO3 and diluted with EtOAc, washed with sat’d NaHCO3 and brine. The organic layer was dried (Na2S04) and concentrated. The crude product was purified by flash chromatography on silica gel with EA/Hex to give .23g of amide. 1H-NMR (400 MHz, CDCI3j delta 5.2 (d, 1 H),6.15 (br., 1 H), 5.68 (br., 1 H), 5.02(br., 1 H), 4.25 (br., 1 H), 3.16(d, 1 H), 2.8 (m, 1 H), 2.7 (t, 1 H), 2.4 (d, 1 H), 1.47 (s, 9H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 128453-98-5. We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; GILEAD SCIENCES, INC.; CAI, Zhenhong, R.; DU, Zhimin; JI, Mingzhe; JIN, Haolun; KIM, Choung, U.; MISH, Michael, R.; PHILLIPS, Barton, W.; PYUN, Hyung-jung; SHENG, Xiaoning, C.; WU, Qiaoyin; ZONTE, Catalin, Sebastian; WO2011/156610; (2011); A2;,
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Downstream synthetic route of 59801-62-6

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 59801-62-6. We look forward to the emergence of more reaction modes in the future.

Thiomorpholine 1,1-dioxide hydrochloride, A common heterocyclic compound, 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., 59801-62-6

A mixture of 3-[2-amino-4-(4-chlorophenyl)-5-thiazolyl]propionic acid (2.67 g), diethyl cyanophosphate (1.69 g), thiomorpholine-1,1-dioxide hydrochloride (1.62 g), triethylamine (2.9 ml) and N,N-dimethylformamide (40 ml) was stirred at room temperature for 3 hrs. The reaction mixture was poured into water, extracted with ethyl acetate, washed with 0.1N aqueous sodium hydroxide solution and water, dried over anhydrous magnesium sulfate and concentrated. The precipitated solid was collected by filtration to give 4-{3-[2-amino-4-(4-chlorophenyl)-5-thiazolyl]propanoyl]thiomorpholine-1,1-dioxide as a colorless powder. Recrystallization from ethanol-isopropyl ether gave colorless prism crystals. melting point: 220-222C.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 59801-62-6. We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; EP1486490; (2004); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

New learning discoveries about 76176-87-9

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 76176-87-9, we look forward to future research findings about .

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 76176-87-9, name is Thiomorpholine-1-oxide hydrochloride. A new synthetic method of this compound is introduced below. 76176-87-9

76176-87-9, To the stirred solution of 3-(4-amino-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutanone (Step S.1 ; 680 mg, 2.05 mmol), 1.2-dichloroethane (55 ml) and diisopropylethylamine (1 .79 ml, 10.25 mmol) was subsequently added 1 -oxo-thiomorpholine hydrochloride (638 mg, 4.10 mmol) and sodium triacetoxyborohydride (652 mg, 3.08 mmol) at 0 C. The reaction mixture was stirred for 1 h at room temperature, and then poured into the stirred mixture of water (150 ml) and EtOAc (150 ml). The precipitate was filtered and washed with water and EtOAc. The solid collected was dried in vacuo to afford the title compound as beige crystals. HPLC-MS: M+H = 432.1 (R, = 0.43); TLC; R, = 0.36 (DCM/MeOH/NH3aq, 200:20:1 ).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 76176-87-9, we look forward to future research findings about .

Reference£º
Patent; NOVARTIS AG; IRM LLC; CHEN, Bai; FAIRHURST, Robin Alec; JIANG, Songchun; LU, Wenshuo; MARSILJE III, Thomas H.; MCCARTHY, Clive; MICHELLYS, Pierre-Yves; STUTZ, Stefan; WO2012/120469; (2012); A1;,
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Thiomorpholine | C4H9NS – PubChem

Analyzing the synthesis route of 114525-81-4

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 114525-81-4, we look forward to future research findings about .

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 114525-81-4, name is (R)-4-(tert-Butoxycarbonyl)thiomorpholine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. 114525-81-4

(Scheme F, F-3: where RF-1 and RF-2 are the same and equal to proton, RF-3 is t-butyl, R5 is 4-[(2,6-dichlorobenzoyl)amino]phenyl and stereochemistry is (R,S)). [C00180] [00425] To a cooled (0-5 C.) solution of Boc-L-thiomorpholine-3-carboxylic acid (Scheme F, F-1: where RF-1 and RF-2 are the same and equal to proton and stereochemistry is (R)) (1.34 g, 5.4 mmol) in methylene chloride (20 mL) was added HOBt (800 mg, 5.94 mmol), DMAP (140 mg, EDC (1.14 g, 5.94 mmol) and triethylamine (2.7 mL, 19.4 mmol). After 10 min, F-2 (Scheme F where RF-1 and RF-2 are the same and equal to proton, RF-3 is t-butyl, R5 is 4-[(2,6-dichlorobenzoyl)amino]phenyl and stereochemistry is (S)) (2.02 g, 4.94 mmol) was added, the reaction allowed to warm to ambient temperature and stirred for 24 h. Volatiles were removed in vacuo and the residue partitioned between methylene chloride and 2.5% aqueous HCl. The organic layer was separated and washed with sat. aqueous NaHCO3, dried and concentrated in vacuo. Purification of the residue by flash chromatography using methylene chloride/ethyl acetate (5%) as eluant afforded the title compound (1.64 g): IR (mull) 1730, 1687, 1667, 1606, 1538, 1515, 1431, 1412, 1395, 1320, 1294, 1258, 1250, 1194, 1158 cm-1; 1H NMR (300 MHz, CDCl3) delta 1.44 (9H), 1.46 (9H), 2.35 (1H), 2.67 (3H), 3.22 (3H), 4.25 (1H), 4.73 (1H), 4.97 (1H), 6.52 (1H), 7.29 (5H), 7.53 (3H); MS (FAB) m/z (rel. intensity) 638 (M+H, 2), Anal. Calcd for C30H37Cl2N3O6S: C, 56.42; H, 5.84; N, 6.58. Found: C, 56.13; H, 5.98; N, 6.58.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 114525-81-4, we look forward to future research findings about .

Reference£º
Patent; Pharmacia & Upjohn Company; Tanabe Seiyaku Co., Ltd.; US6685617; (2004); B1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

Downstream synthetic route of Thiomorpholine-1-oxide hydrochloride

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 76176-87-9, we look forward to future research findings about .

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 76176-87-9, name is Thiomorpholine-1-oxide hydrochloride. A new synthetic method of this compound is introduced below. 76176-87-9

TBTU (176 mg, 0.55 mmol) was added in one portion to a stirred solution of 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (125 mg, 0.27 mmol) and DIPEA (0.286 mL, 1.64 mmol) at room temperature and stirred for 2.5 h. Thiomorpholine 1-oxide hydrochloride (85 mg, 0.55 mmol) was added to the reaction mixture and stirring was continued for 3 h. The reaction mixture was diluted with DCM, washed with water, brine, dried over MgSO4 and concentrated. The residue was purified by preparative HPLC. The fractions were evaporated to dryness, the residue was dissolved in DCM, dried over MgSO4 and concentrated. The remaining solid was triturated with diethyl ether, filtered, washed with diethyl ether and dried under vacuum at 50 C. to afford 8-[1-(3,5-difluorophenyl)pyrrolidin-2-yl]-2-morpholino-6-(1-oxo-1,4-thiazinane-4-carbonyl)chromen-4-one (87 mg, 57%) as a pale beige solid.Mass Spectrum:m/z [M+H]+=558.Proton NMR Spectrum:(DMSO-d6) 1.75-1.86 (m, 1H), 1.98-2.08 (m, 2H), 2.14 (bs, 0.5H), 2.51-2.58 (m partially hidden by DMSO-d5, 1H), 2.64 (bs, 1H), 2.81 (bs, 1.5H), 2.98 (bs, 1H), 3.27 (bs, 1H), 3.40 (bs, 1H), 3.49-3.65 (m, 5H), 3.64-3.83 (m, 6H), 4.21 (bs, 0.5H), 4.34 (bs, 0.5H), 5.25 (d, 1H), 5.62 (s, 1H), 6.13 (d, 2H), 6.34 (t, 1H), 7.18 (s, 1H), 7.87 (d, 1H)

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 76176-87-9, we look forward to future research findings about .

Reference£º
Patent; ASTRAZENECA AB; US2012/264731; (2012); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

Downstream synthetic route of Thiomorpholine 1,1-dioxide

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 39093-93-1, we look forward to future research findings about .

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 39093-93-1, name is Thiomorpholine 1,1-dioxide. This compound has unique chemical properties. The synthetic route is as follows. 39093-93-1

To a solution of 2-(4-(bromomethyl)phenyl)-4,4,5 ,5 -tetramethyl- 1,3,2-dioxaborolane (0.50 g, 1.68 mmol) in DMF (8 mL) were added K2C03 (0.58 g, 4.21mmol) and thiomorpholine 1,1-dioxide (0.27 g, 2.02 mmol). The reaction mixture was stirred at rt for 2 h. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated and washed with brine, dried over MgSO4. The filtrate was concentrated in vacuo to give the title compound as a white solid (0.53 g, 89%). ?H NMR(DMSO-d6) oe 7.65 (d, J= 8.1 Hz, 2 H), 7.35 (d, J= 7.9 Hz, 2 H), 3.68 (s, 2 H), 3.16 -3.01 (m, 4 H), 2.85 (dd, J 6.2, 4.0 Hz, 4 H), 1.29 (s, 12 H); MS(ESIj mlz 352.1 (M + H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 39093-93-1, we look forward to future research findings about .

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; KIM, Kyoung S.; ZHANG, Liping; PURANDARE, Ashok Vinayak; SEITZ, Steven P.; WO2015/77193; (2015); A1;,
Thiomorpholine – Wikipedia
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Some tips on 39093-93-1

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 39093-93-1. We look forward to the emergence of more reaction modes in the future.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.39093-93-1, Thiomorpholine 1,1-dioxide it is a common compound, a new synthetic route is introduced below., 39093-93-1

i) (1,1-Dioxo-1,6-thiomorpholin-4-yl)-{6-[3-(5-fluoro-pyridin-2-yl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridin-3-yl}-methanone; To a solution of 6-((3-(5-fluoropyridin-2-yl)-5-(hydroxymethyl)isoxazol-4-yl)methoxy)nicotinic acid (384 mg, 1.11 mmol) in DMF (10 mL) was added thiomorpholine 1,1-dioxide (165 mg, 1.22 mmol), N,N,N’,N’-tetramethyl-O-(benzotriazole-1-yl)-uronium tetrafluoroborate (393 mg, 1.22 mmol) and N,N-diisopropyl ethylamine (0.95 mL, 5.56 mmol). The reaction mixture was stirred for 30 min at room temperature. After evaporation of the solvent the residue purified by chromatography (silica, ethylacetate_heptane=1:1 to 1:0) to afford the title compound (422 mg, 82percent) as a white solid. MS: m/e=463.2 [M+H]+., 39093-93-1

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 39093-93-1. We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; Buettelmann, Bernd; Gabriel, Stephen Deems; Hanlon, Steven Paul; Jakob-Roetne, Roland; Lucas, Matthew C.; Spurr, Paul; Thomas, Andrew; Waldmeier, Pius; US2010/256127; (2010); A1;,
Thiomorpholine – Wikipedia
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Analyzing the synthesis route of 134676-67-8

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 134676-67-8, we look forward to future research findings about .

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 134676-67-8, name is N-Boc-2-thiomorpholinecarboxylic Acid. A new synthetic method of this compound is introduced below. 134676-67-8

T3P (3.61 mL, 6.07 mmol) was added to a solution of 4-amino-2-chlorobenzonitrile (370 mg, 2.43 mmol), 4-(tert-butoxycarbonyl)thiomorpholine-2-carboxylic acid (500 mg, 2.02 mmol), DIEA (1.76 mL, 10.11 mmol) and DMAP (272 mg, 2.22 mmol) in ethyl acetate (10 mL) at room temperature, and the mixture was heated at 60C overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent gradient; 5?60% ethyl acetate/hexane) to give tert-butyl 2-((3-chloro-4-cyanophenyl)carbamoyl)thiomorpholine-4-carboxylate (765 mg, 2.003 mmol, 99%) as an orange oil. 1H NMR (300 MHz, CDCl3):delta 1.38-1.55(9H,m), 2.46-2.64(1H,m), 2.74-2.87(1H,m), 3.34-3.52(2H,m), 3.65(1H,dd,J=14.2,2.8 Hz), 4.03-4.17(1H,m), 4.60(1H,dd,J=14.2,4.0 Hz), 7.60(2H,d,J=3.8 Hz), 7.94(1H,s), 9.14(1H,brs)., 134676-67-8

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 134676-67-8, we look forward to future research findings about .

Reference£º
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; ODA, Tsuneo; IMADA, Takashi; KONO, Mitsunori; SATO, Ayumu; TOMATA, Yoshihide; OCHIDA, Atsuko; ISHII, Naoki; SASAKI, Yusuke; FUKASE, Yoshiyuki; YUKAWA, Tomoya; FUKUMOTO, Shoji; (200 pag.)EP3192791; (2017); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem