Tag: M.W=100-200

Reference of 93919-56-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 93919-56-3 name is (4-(Trifluoromethoxy)phenyl)methanamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(i) N-[4-(Trifluoromethoxy)benzyl]acetamide To a solution of 4-(trifluoromethoxy)benzylamine (3.46 g, 57.6 mmol) in DMF (75 mL) and acetic acid (10.0 g, 52.3 mmol) at -10 C. were added O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate (20.2 g, 62.8 mmol) and N,N-diisopropylethylamine (20.0 mL, 115 mmol) and the reaction mixture was stirred at room temperature overnight. Ethyl acetate (200 mL) was added and the organic phase was washed with water (100 mL), 0.25 M NaOH (100 mL), saturated aqueous NaHCO3 (100 mL), water (100 mL), 0.5 M HCl (100 mL), and water (100 mL), dried over MgSO4, and concentrated in vacuo to afford 11.2 g (92%) of a colourless oil. 1H NMR (600 MHz, CDCl3): delta 2.03 (s, 3H), 4.43 (d, 2H), 5.83 (bs, 1H), 7.17 (d, 2H), 7.31 (d, 2H). 13C NMR (125 MHz, CDCl3): delta 22.9, 42.8, 120.5 (q), 121.1, 129.0, 137.3, 148.4, 170.6.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (4-(Trifluoromethoxy)phenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; Alstermark, Eva-Lotte Lindstedt; Olsson, Anna Christina; Li, Lanna; US2005/282822; (2005); A1;,
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Synthetic Route of 16452-01-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 16452-01-0 name is 3-Methoxy-4-methylaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of 0.339 g (2 mmol) 2-Chlorobenzthiazole (commercially available) and 0.275 g (2 mmol) 3-methoxy-4-methylaniline (commercially available) in 4 ml acetic acid was heated to 115 C. for 4 h. After cooling to room temperature the mixture was subjected to preparative HPLC separation on reversed phase eluting with an acetonitrile/water gradient. The product fractions of Benzothiazol-2-yl-(3-methoxy-4-methyl-phenyl)-amine were evaporated to dryness and reacted according to the procedure described for Example 2 with 2-chlorobenzoyl chloride to yield the title compound. MS (m/e): 409.3 (MH+, 100%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-4-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; Nettekoven, Matthias Heinrich; Roever, Stephan; US2004/266845; (2004); A1;,
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Application of 33311-29-4,Some common heterocyclic compound, 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, molecular formula is C9H13NO2, 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.

[00511] To a solution of tert-butyl 3-(2-chloro-5-nitropyrimidin-4-ylamino )phenylcarbamate(1) (430 mg, 1.37 mmol) in THF (10 mL) was added DIEA (530 mg, 4.1 mmol) and 4-(2-methoxyethoxy)aniline (39) (274 mg, 1.64 mmol) at r.t. under N2 atmosphere. The resultingmixture was stirred at r.t. overnight. The solvent was removed and the residue was purified byflash column chromatography (silica gel, 0 to 5% ethyl acetate in PE/DCM (1/1), with 0.5%TEA) to provide tert-butyl 3-(2-( 4-(2-methoxyethoxy)phenylamino )-5-nitropyrimidin-4-ylamino)phenylcarbamate (2) (559 mg, 96%) as a yellow solid. LC-MS (ESI) m/z (M+1) 497.1.

The synthetic route of 33311-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACYCLICS, INC.; CHEN, Wei; YAN, Shunqi; LOURY, David, J.; FRYE, Leah, Lynn; GREENWOOD, Jeremy, Robert; SHELLEY, Mee, Yoo; WANG, Longcheng; WO2014/130693; (2014); 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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C7H6F3NO

General procedure: 1-Aryl-4-nitro-1H-imidazoles were prepared following the general procedure we have developed in our laboratory [23] with some slight modifications. Equimolar amount of aniline derivative was treated with 1,4-dinitro-1H-imidazole in aqueous methanol at ambient temperature in the dark for several hours until complete disappearance of 1,4-dinitro-1H-imidazole monitored by TLC. In some cases, the mixture was heated under reflux to complete the reaction. On cooling, the desired crude 1-aryl-4-nitro-1H-imidazoles separated from the mixture by precipitation. After filtration and recrystallization the pure product was obtained. Yields, solvents used for recrystallization and specific data are given below in the respective sections. Further details are available on request.

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; Trunz, Bernadette Bourdin; Jdrysiak, Rafa?; Tweats, David; Brun, Reto; Kaiser, Marcel; Suwi?ski, Jerzy; Torreele, Els; European Journal of Medicinal Chemistry; vol. 46; 5; (2011); p. 1524 – 1535;,
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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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H17NO2

General procedure: 3.2. Reaction of Wang Resin 1 with Trichloroacetonitrile and Fmoc-amino Alcohol (Resin 2)Wang resin 1 (1 mmol/g loading, 1 g) was suspended in 10 mL of anhydrous DCM, then 1.5 mL oftrichloroacetonitrile was added, and the resin was left in a freezer for 30 min. Next, a solution of 100 Lof DBU in 2 mL of anhydrous DCM was added, and the slurry was shaken for 1 h. The resin waswashed with anhydrous DCM (3) and anhydrous THF (3). The solution of Fmoc-amino alcohol(3 mmol) in 10 mL of anhydrous THF was added to the resin, followed by the dropwise addition of63 L of a solution of BF3Et2O, and the slurry was shaken for 30 min. Resin 2 was washed THF (3),MeOH (3), and DCM (5). A sample of the resin was washed with MeOH (3) and dried, and10 mg was cleaved with 50% TFA for 30 min, and the product quantified (Fmoc absorbance at 300 nm).Typical loading was between 0.35-0.50 mmol/g.3.3. Acylation with a-Bromocarboxylic Acids (Resins 3 And 13)Resin 2 (1 g) was washed with DCM and DMF, Fmoc was deprotected with 50% piperidine inDMF for 15 min, and the resin was washed with DMF (3) and DCM (5). Reaction of the resinwith a solution of -bromocarboxylic acid (5 mmol) in 10 mL of DCM was carried out in a syringewith a frit, and DIC (2.5 mmol, 386 L) was added. After 5 min, DIU was filtered, and the solutionwas transferred to the syringe with resin 1 and shaken for 1 h. When bromoacetic acid was used,DIEA (2.5 mmol, 436 L) was also added. Then, the resin was washed with DCM (3)._ 3.4. Reaction with Amino-aldehyde Dialkyl Acetal and N-Derivatization (Resin 4)Resin 3 (1 g) was washed with DMF (3), a solution of amino-aldehyde dialkyl acetal (10 mmol)and DIEA (10 mmol, 1.74 mL) in 10 mL of DMF was added, and the slurry was shaken for 2 h.An analytical sample was taken for analysis, reacted with 0.5 M Fmoc-OSu in DCM for 1 h and cleavedwith 50% TFA for 30 min.Resin from the previous step was split into four 250 mg portions, which were washedwith reaction solvent: DCM for sulfonamides (Ns-Cl, Tos-Cl) (1 mmol) and DMSO for 4-fluoro-3-nitrobenzotrifluoride (1 mmol). Then, 3 mL of the reaction solvent and DIEA (1.8 mmol, 174 L) wasadded, and the slurry was shaken for 2 h (in the case of sulfonamides) or overnight (in the case of4-trifluoromethyl-2-nitroaryl). Resin 4 was washed with the reaction solvent (3) and then DCM (3).A sample for analysis was reacted with 0.5 M Fmoc-OSu in DCM for 1 h and cleaved with 50% TFA for30 min.

The synthetic route of 41365-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gimenez-Navarro, Vanesa; Krch?ak, Viktor; Molecules; vol. 23; 5; (2018);,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6298-96-0 as follows. SDS of cas: 6298-96-0

To a 250 mL RBF was added (S)-1-(4-methoxyphenyl)ethanamine (6.39 g, 42.3 mmol), 1-(3- methylpyridin-2-yl)ethanone (6 g, 44.4 mmol), DCM (Volume: 106 ml) and STAB-H (17.92 g, 85 mmol) at rt and the reaction was stirred for 24h. The reaction was quenched by the addition of 1N NaOH until a pH of 8 was achieved. The phases were separated and the organic layer was treated with 1N NaOH until pH 11 was observed. The DCM layer was dried with MgSO4 filtered and concentrated to an oily residue. The residue was purified via combiflash to separate the diastereomers (~4:1 by crude NMR, 80g column 10-30% gradient over 40 min). 1H NMR (400 MHz, CDCl3): delta= 8.45 (d, J= 4.8 Hz, 1H), 7.34 (d, J= 7.6 Hz, 1H), 7.13 (d, J= 8.5 Hz, 2H), 7.04 (dd, J= 7.8, 4.6 Hz, 1H), 6.82 (d, J= 9.2 Hz, 2H), 3.79 (s, 3H), 3.74 (q, J= 6.0 Hz, 1H), 3.27 (q, J= 5.9 Hz, 1H), 1.24 (d, J= 6.3 Hz, 3H), 1.20 (d, J= 6.3 Hz, 3H); LC/MS 75% MeOH in H2O over 3 minutes, rt = 0.480 at 254 nM, MS (+) 271.2

According to the analysis of related databases, 6298-96-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; WILSON, Robert James; NGUYEN, Huy Hoang; KIM, Michelle Bora; WILSON, Lawrence; MILLER, Eric James; TAHIROVIC, Yesim Altas; TRUAX, Valarie; KAISER, Thomas; (311 pag.)WO2018/156595; (2018); A1;,
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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. 22483-09-6, name is 2,2-Dimethoxyethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C4H11NO2

(a) Ethyl N-(2,2-dimethoxyethyl)-carbamate 214 g (2 mol) of ethyl chloroformate are added dropwise to 214 g (2 mol) of aminoacetaldehyde dimethyl acetal in 1 l of toluene and 90 g of NaOH in 500 ml of water at 10 C. The mixture is stirred at room temperature for a further 2 hours and the aqueous phase is separated off, saturated with sodium chloride and extracted with toluene. The toluene solutions are dried over magnesium sulphate and concentrated and the residue is distilled. Yield: 338 g (95.4% of theory) Boiling point: 60 C./0.03 mbar

The synthetic route of 22483-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US4990517; (1991); A;,
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Synthetic Route of 592-55-2, These common heterocyclic compound, 592-55-2, name is 1-Bromo-2-ethoxyethane, 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.

Example 2: 4- {3-Hydroxy-3- [4- (2-ethoxyethoxy)-5, 5, 8, 8- tetramethyl-5,6, 7, 8-tetrahydronaphth-2-yl] prop-1-ynyl}- benzoic acid; a. 5,5, 8, 8-Tetramethyl-4- (2-ethoxyethoxy)- 5,6, 7,8-tetrahydronaphthalene-2-carbaldehyde 36 g (156 mmol) of 4-hydroxy-5,5, 8,8-tetra- methyl-5,6, 7, 8-tetrahydronaphthalene-2-carbaldehyde are dissolved in 400 mL of anhydrous DMF. 6.5 g (163 mmol) of 60% sodium hydride are added portionwise and the reaction medium is stirred for 1 hour. 25 g (163 mmol) of 2-ethoxyethyl bromide are added portionwise and the medium is stirred at room temperature for 2 hours and then hydrolysed and extracted with ethyl ether. The organic phase is washed with 1N sodium hydroxide solution, and then three times with water. The residue obtained is purified by chromatography (eluent: heptane). A yellow oil is obtained (m = 40.7 g; yield = 86%).

The synthetic route of 592-55-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2005/56510; (2005); A2;,
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Reference of 929-75-9, A common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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.

General procedure: All macrocyclic compounds were obtained as previously described. 20,21 The corresponding diester (1-3) (10 mmol) and diamine (4-8) (10 mmol) were dissolved in MeOH (100 ml). The reaction mixture was stirred for 7 d at rt. After completion of the reaction (monitored by TLC), the solvent was evaporated and the residue was puriofied by chromatography on a silica gel column using 0-5% solutions of MeOH/CH2Cl2. Analytical and spectroscopic data are collected in the Supplementary Materials.

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; Pikus, Grzegorz; Pa?niczek, Ewa; Jurczak, Janusz; Arkivoc; vol. 2017; 2; (2017); p. 534 – 545;,
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Electric Literature of 20781-20-8, 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2,4-dimethoxybenzylamine (6.6 mL, 43.5 mmol) in DCM (85 mL) was added saturated aqueous sodium bicarbonate solution (85 mL) and the mixture was stirred vigorously at RT for 15 min. Stirring was stopped then thiophosgene (6.6 mL, 87 mmol) was added via syringe to the bottom layer. The mixture was stirred at RT for 90 min then the aqueous layer was separated and the organic layer was washed with brine, dried over Na2SC>4 and concentrated in vacuo twice from DCM to give 9.1 g of l-(isothiocyanatomethyl)-2,4-dimethoxybenzene as yellow oil.

The synthetic route of (2,4-Dimethoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCKITTRICK, Brian; CALDWELL, John, P.; MCCAULEY, John, A.; VACCARO, Henry; CHAN, Tin-Yau; KIM, Hyunjin; SMITH, Elizabeth; HONG, Liwu; KHAN, Tanweer; YING, Shihong; WANG, Hongwu; (66 pag.)WO2018/118827; (2018); A1;,
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