Category: ethers-buliding-blocks

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. 767-91-9, name is 2′-Methoxyphenyl acetylene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

General procedure: To a mixture of alpha-azidoamide 16aa (34 mg, 0.20 mmol) and phenylacetylene (9a; 24 L,0.20 mmol) in t-BuOH/H2O (2 mL, 1:1) were added 0.5 M CuSO4 (0.020 mL, 0.010 mmol) and 1.0 M sodium ascorbate (0.020 mL, 0.020 mmol). The reaction mixture was stirred at room temperature for 1 day, and then the resulting reaction mixture was filtered. The separated solid was washed with H2O and hexanes, and triturated with hexane/EtOAc (10:1) to give the 1-morpholino-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanone (2aaa; 52 mg, 96%) as a white solid

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

Reference:
Article; Lee, Doohyun; Kim, Daehun; Lee, Seungyeon; Kim, Taegeum; Kim, Joobin; Kim, Sohee; Liu, Kwang-Hyeon; Lee, Sangkyu; Bae, Jong-Sup; Song, Kyung-Sik; Cho, Chang-Woo; Son, Youn Kyung; Baek, Dong Jae; Lee, Taeho; Molecules; vol. 20; 11; (2015); p. 19984 – 20013;,
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Electric Literature of 38336-04-8,Some common heterocyclic compound, 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, molecular formula is C9H13NO, 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.

To a solution of(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyl triacetate (9.8 g, 25 mmol) in dichloromethane (100 mL) was added 128 (4 g, 26 mmol) at 0 C. After stirred for 2 hours, trifluoro acetic acid (15.4 g, 159 mmol) was added. The resulting solution was stirred for 12 hours at room temperature, then quenched with ice- water (200 mL) and neutralized by the addition ofNaHCC”3 (26 g, 318 mmol). The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (2×100 mL), dried over anhydrous sodium sulfate, and concentrated under vacuum to give a residue, which was purified by silica gel column, eluted with 10 % – 50 % ethyl acetate in petroleum ether to afford 129 as a white syrup (9.8 g, 77 %). (ES, m/z) [M+H]+ 481.0; 1H NMR (300 MHz, CDC13) delta 7.31 – 7.38 (m, 5H), 6.24 (d, / = 6.3 Hz, 1H), 5.41 – 5.43 (m, 1H), 4.94 – 4.98 (m, 1H), 4.55 (s, 2H), 4.34 – 4.37 (m, 1H), 4.14 – 4.16 (m, 3H), 3.83 – 3.87 (m, 1H), 3.64 (t, / = 5.4 Hz, 2H), 3.53 (t, / = 5.1 Hz, 2H), 2.12 (s, 3H), 2.10 (s, 3H), 2.09 (s, 3H).

The synthetic route of 38336-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALECTOS THERAPEUTICS INC.; MERCK SHARP & DOHME CORP.; CHANG, Jiang; LIU, Kun; MCEACHERN, Ernest J.; MU, Changwei; SELNICK, Harold G.; SHI, Feng; VOCADLO, David J.; WANG, Yaode; WEI, Zhongyong; ZHOU, Yuanxi; ZHU, Yongbao; WO2012/62157; (2012); A1;,
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Application of 60792-79-2,Some common heterocyclic compound, 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, molecular formula is C4H14Cl2N2O, 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 7 Preparation of 5-((2-(2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)ethoxy)ethyl)carbamoyl)-2-methylpyrazine 1-oxide (I-4) In a typical run, sodium hydroxide (400 mg, 10 mmol) was dissolved in MeOH (70 mL) and 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol) was added. The resulting reaction mixture was stirred at room temperature for 30 min A solution containing Boc2O (740 mg, 3.40 mmol) in THF (15 mL) was then added dropwise, at room temperature, over a period of 15 min. The resulting reaction mixture was stirred at room temperature for 18 h. It was then concentrated under reduced pressure. The resulting residue was taken up in CH2Cl2 (200 mL) and stirred vigorously at room temperature for 4 h. The mixture was filtered and the filtrate was concentrated under reduced pressure to afford tert-butyl 2-(2-aminoethoxy)ethylcarbamate (850 mg, 74%).

The synthetic route of 60792-79-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Vu, Chi B.; US2011/82156; (2011); A1;,
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Related Products of 7664-66-6, A common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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.

To a solution of compound Al (0.5 g, 065 mmol) in toluene (10 rnL) and 4- Isopropoxyaniline (202 mg, 134 mmol) was added Ti(O-iPr)4 (190 mg, 0.66 rnmol). Themixture was stirred at 120 C overnight. The mixture was quenched with H20 (50 mL) and extracted with DCM (20 mE x 3). The combined organic layer was dried over potassium carbonate, filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH == 15/1) to afford the crude products 304 and 30-2 (140 rng) as a brown solid .LC-MS: rnz 899.2 [M+H]?. To a solution of compounds 304 and 30-2 (137 mg. 015 rnmoi) in DCM (5 mE) was added DAST (24.5 rng, 0.15 mrnoi) at -78 C underN2. After stirred at -78 C for I Ii, the mixture was quenched with aqueous NaHCO3 and H20 and then extracted with DCM (30 mL x 3). i1e combined organic layer was dried over potassium carbonate, filtered and concentrated. The residue was purified by prep-HPLC to afford compound 30 (19 mg, yield14%) as yellow solid. Partial ?H NMR (CDCi3, 400 MHz): 6.93 (d, J::: Hz, 2H), 6.78-6.75 (m, 3H), 4.88 (s, 1H), 4.71-4.66 (in, 1H), 4.46-4.33 (rn, 2H), 4,32-4.29 (m, IH), 3.66-3.63 (m, 1H). 3.29-3.26 (m, 2H), 3.13-3.09 (in. 2H), 3.56-2.33 (rn, 3H); EC-MS: m/z 81.2[M+l-[[5.

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGRIMETIS, LLC; CALABRESE, Andrew; (110 pag.)WO2018/132288; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 41406-00-2, name is 3-Isopropoxyaniline, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 41406-00-2, Safety of 3-Isopropoxyaniline

To a stirred solution of 2,6,6-trimethylcyclohex-l-enecarbaldehyde (99.5 mg, 0.66 mmol) in methanol (2 mL) ) was added 3-isopropoxyaniline (99.5 mg, 0.66 mmol) followed by acetic acid (0.1 mL), and sodium cyanoborohydride (124.0 mg, 1.97 mmol). The reaction was stirred at room temperature for 2 hours. The reaction was quenched by addition of saturated aqueous ammonium chloride (5 mL) and the organic volatiles were evaporated under reduced pressure. The resulting mixture was diluted with ethyl acetate (30 mL) and the organic phase was washed with water (20 mL), saturated aqueous sodium bicarbonate (20 mL) and brine (20 mL), dried over anhydrous sodum sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 90/1 ) to give the title compound as a colorless oil (137 mg, Yield: 72%). Rf = 0.6 (20:1 petroleum ether/ethyl acetate); H NMR (400 MHz, CDCI3) delta 7.05 (t, J = 8.0 Hz, 1 H), 6.24-6.18 (m, 2 H), 6.15-6.14 (m, 1 H), 4.56-4.50 (m, 1 H), 3.55 (s, 2 H), 3.30 (bs, 1 H), 1.97 (t, J = 6.2 Hz, 2 H), 1.66 (s, 3 H), 1.66-1.59 (m, 2 H), 1.50-1.43 (m, 2 H), 1.33 (d, J = 6.0 Hz, 6 H), .02 (s, 6 H) ppm; Mass spectrum (ESI +ve) m/z 288 (M + H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Isopropoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; BIKAM PHARMACEUTICALS, INC.; QUACH, Tan; BERMAN, Judd; GARVEY, David, S.; WO2013/81642; (2013); A1;,
Ether – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 109-85-3, name is 2-Methoxyethylamine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 109-85-3, Safety of 2-Methoxyethylamine

The starting material for the preparation of (RS)-N-{4-CARBAMIMIDOYL-2-[(2-METHOXY- ethylcarbamoyl)-methoxy]-benzyl}-2-(2, 6-difluoro-4-methoxy-phenyl)-2-ethoxy- acetamide hydrochloride, 2-chloro-N- (2-methoxy-ethyl)-acetamide, was prepared from chloroacetyl chloride with 2-methoxyethyl amine and triethylamine in CHZCL2.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Methoxyethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/48335; (2004); A2;,
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Application of 437-82-1,Some common heterocyclic compound, 437-82-1, name is 2,6-Difluoroanisole, molecular formula is C7H6F2O, 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.

The 2,6-difluoroanisole (4.00 ml, 33 . 9mmol) and sodium iodide (15.0g, 100mmol) dissolved in acetonitrile (50 ml) , trimethylchlorosilane (8.80 ml, 102mmol) is also added and heated to 100 C for 5 hours. Cooling to room temperature, reducing pressure and evaporating solvent, adding water (40 ml), dichloromethane is used for (30 ml × 3) extraction. Combined with the phase, with water (40 ml), saturated salt water (40 ml) washing, dry anhydrous sodium sulfate. Filtering, evaporating solvent under reduced pressure, the crude product purification column chromatography (petroleum ether/ethyl acetate (v/v)=6/1), to get the yellow oil (2.2g, 50%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Difluoroanisole, its application will become more common.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Zhuo, Yinglin; Wang, Xiaojun; Zhang, Yingjun; Wen, Liang; Wu, Shoutao; Yuan, Xiaofeng; (87 pag.)CN105384687; (2016); A;,
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Related Products of 3616-56-6, 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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis Example B13Synthesis of 3-bromo-12H-benzofuranyl[3,2-a]carbazole (compound 13)Under nitrogen, compound 12 (3.2 g, 1 eq) is initially charged and dissolved with acetic acid (30 ml) while heating to reflux.Then (dimethylamino)acetaldehyde diethyl acetal (95percent; 21.9 g, 10 eq.) is added dropwise to the reaction within 1 h and the mixture is stirred at reflux for 48 h.The mixture is cooled to room temperature and diluted with methylene chloride.Washed in a separating funnel with distilled water and then with saturated NaCl solution.The organic phase is dried with sodium sulfate and concentrated. LC (SiO2, 3:1 cyclohexane/methylene chloride) gives 0.98 g of product (28.6percent yield).1H NMR (CD2Cl2, 400 MHz): delta=8.75 (s, 1H), 8.24 (s, 1H), 8.1 (dd, 2H), 7.67 (d, 1H), 7.48-7.55 (m, 6H).

The synthetic route of 2,2-Diethoxy-N,N-dimethylethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; OSRAM OPTO SEMICONDUCTORS GMBH; KONINKLIJKE PHILIPS ELECTRONICS N.V.; US2011/266528; (2011); A1;,
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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. 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, A new synthetic method of this compound is introduced below., name: 4-(Benzyloxy)-3-fluoroaniline

4-Benzyloxy-3-fluoro-aniline (55 g), isopropyl alcohol (550 ml) and (R)-glycidyl butyrate (36.6 g) were taken into a reaction flask at room temperature (25-30C), and the resulting mass was heated to reflux and then stirred for 28 hours at the same temperature. After completion of the reaction, the solvent was distilled under vacuum to obtain a residue. Diisopropyl ether (560 ml) was added to the residue at the room temperature and theresulting solution was heated to reflux, followed by stirring for 15 minutes at the same temperature. The reaction mass was cooled to 25-30C and then stirred for 30 minutes at the same temperature. The separated solid was filtered and then washed with diisopropyl ether (100 ml) to produce 62 g of (2R)-3-(4-benzyloxy-3-fluoro-phenylamino)-2-hydroxy- propyl butanoate (Purity by HPLC: 98.6%).

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

Reference:
Patent; SYMED LABS LIMITED; MOHAN RAO DODDA; MALLA REDDY VANGA; JITHENDER AADEPU; (95 pag.)WO2016/79757; (2016); A2;,
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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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, A new synthetic method of this compound is introduced below., Quality Control of Perfluoro(2-methyl-3-oxahexanoyl) fluoride

EXAMPLE 1; Example of production of monomer (1M); EXAMPLE 1-1: Esterification reaction; [] 2-Tetrahydrofurfuryl alcohol (20 g) and (CH3CH2)3N (21.8 g) were put in a flask and stirred under cooling with ice. While keeping the temperature in the flask to at most 10C, FCOCF(CF3)OCF2CF2CF3 (71.5 g) was dropwise added over a period of 1 hour. After completion of the dropwise addition, stirring was further carried out at 25C for 2 hours. Then, while keeping the temperature in the flask to at most 15C, water (50 mL) was added to obtain a reaction liquid which was separated into two layers. The reaction liquid was separated, and the lower layer was washed with water (50 mL) twice and dried over magnesium sulfate, followed by filtration to obtain a crude liquid. By distillation under reduced pressure, an aimed ester compound (66.3 g) was obtained as a fraction of 88 to 89C/2.7 kPa (absolute pressure). The GC purity was 98%. Formation of compound (A-20) was confirmed by NMR analysis. 1H-NMR (300.4 MHz, CDCl3, TMS) delta (ppm) : 1.60 to 1.73 (m, 1H), 1.86 to 2.10 (m,3H), 3.76 to 3.91 (m,2H), 4.14 to 4.22 (m, 1H), 4.28 to 4.47 (m,2H). 19F-NMR (282.7 MHz, CDCl3, CFCl3) delta (ppm): -79.9 (1F), -81.3 (3F), -82.1 (3F), -86.4 (1F), -129.5 (2F), -131.5 (1F).

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

Reference:
Patent; ASAHI GLASS COMPANY LTD.; EP1548014; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem