Month: July 2021

Related Products of 59557-91-4, The chemical industry reduces the impact on the environment during synthesis 59557-91-4, name is 4-Bromo-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 3k (300 mg, 1.48 mmol) in anhydrous CH2C12 (15 mL) was added pyridine (0.24 mL, 2.97 mmol) and 1-propanesulfonyl chloride (0.18 mL, 1.63 mmol) under argon, and the mixture was stirred at room temperature for 16 h. After being quenched with 1 N HC1(aq) (1.0 mL), water, and CH2C12 were added, the layers were separated. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel (EtOAc/hexane, 10:90 to 15:85) to give 6k (490.1 mg, 99%) as a light yellow oil; ?H NMR (CDC13, 500 MHz) 7.41 (1 H, d, J = 8.6 Hz), 7.08 (1 H, dd, J = 8.3, 2.3 Hz), 7.03 (1 H, d, J = 2.5 Hz), 6.74 (1 H, br) , 3.88 (3 H, s), 3.02-2.98 (2 H, m), 1.83-1.79 (2 H, m), 1.00 (3 H, t, J = 7.4 Hz); ?3C NMR (CDC13, 125 MHz) 149.5, 125.5, 124.2, 121.0, 117.5, 114.3, 56.1, 53.1, 17.1, 12.8.

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, 4-Bromo-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF HOUSTON SYSTEM; TRUSTEES OF TUFTS COLLEGE; CUNY, Gregory; SUEBSUWONG, Chalada; DEGTEREV, Alexei; (139 pag.)WO2018/183633; (2018); A1;,
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These common heterocyclic compound, 4393-09-3, name is (2,3-Dimethoxyphenyl)methanamine, 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. name: (2,3-Dimethoxyphenyl)methanamine

Step A. tert-Butyl 4-[(1-{[(2,3-dimethoxybenzyl)amino]carbonyl}-4-piperidinyl)amino]phenethylcarbamate The title compound (0.32 g, 0.64 mmol) was prepared from 2,3-dimethoxy benzyl amine (0.668 g, 4.0 mmol) and {2-[4-(piperidin-4-ylamino)-phenyl]-ethyl}-carbamic acid tert-butyl ester (1.276 g, 4.0 mmol) according to Procedure C.

The synthetic route of (2,3-Dimethoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; US2002/28832; (2002); 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. 41406-00-2, name is 3-Isopropoxyaniline, A new synthetic method of this compound is introduced below., name: 3-Isopropoxyaniline

A mixture of 2,4-dichloro-5-methylpyrimidine (0.326 g, 2.0 mmol), 3-isopropoxyaniline (0.310 mL, 2.1 mmol), DIPEA (0.420 mL, 2.4 mmol), and iPrOH (2 mL) was allowed to react and worked up following the same procedure used to make RJ1-048, with the exception that no MeOH was added before workup and that the reaction was run overnight for 19.5 hours. The residue was then purified via flash chromatography, and the desired product RJl-058 was collected at hexanes/EtOAc 15-20% as a flaky caramel-colored solid (0.242 g, 44%). m.p. = 127 – 128 C. NMR (400 MHz, DMSO-ifc) delta 8.76 (s, 1H), 8.03 (s, 1H), 7.30 (t, / = 2.2 Hz, 1H), 7.25-7.13 (m, 2H), 6.64 (ddd, / = 8.0, 2.4, 1.1 Hz, 1H), 4.59^.50 (m, 1H), 2.15 (d, / = 0.6 Hz, 3H), 1.27 (d, / = 6.0 Hz, 6H). LRMS (ESI+) m/z 278.1 (M35C1+H)+, 280.1 (M37C1+H)+; HRMS (ESI+) m/z calculated for CwHieClNsO (M+H)+ 278.10547, found 278.10860.

The synthetic route of 41406-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)benzene, 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 1663-61-2, SDS of cas: 1663-61-2

General procedure: Method B (synthesis of 1,2,4-triazin-6(5H)-ones 2) ? The appropriate alpha-aminocarboxylic acid hydrazide 5 (10 mmol) was added to a mixture of triethyl orthoester (10 mmol), dry xylene (40 mL) and 0.12 g p-TsOH and kept under reflux until the disappearance of the starting hydrazide 5 was completed (2-6 h). After cooling, the mixture was washed with water (30 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude product was purified by column chromatography with silica gel and an eluent of benzene/AcOEt, 1:3 v/v or MeOH/CHCl3, 1:4 v/v.

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

Reference:
Article; Kudelko, Agnieszka; Zielin?ski, Wojciech; Jasiak, Karolina; Tetrahedron Letters; vol. 54; 35; (2013); p. 4637 – 4640;,
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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 109-85-3 as follows. SDS of cas: 109-85-3

A) Chloro(N-(2-methoxyethyl))acetamide, (1) In a three-necked 2L round bottom flask fitted with two 500mL addition funnels, containing 56.4g (39.8mL, 0.50mole) chloroacetyl chloride in 400mL dichloromethane and 20g (0.50mole) sodium hydroxide in 400mL water, respectively, and a water-cooled condenser, was placed 35.7g (41.3mL, 0.48mole) 2-methoxyethylamine, 100mL water, 100mL dichloro-methane. The reaction vessel was cooled to 0 C. by a salt-ice bath. The organic and aqueous solutions were allowed to add slowly, -0.25mL per minute, to the reaction mixture. During the addition the pH of the water phase of the reaction was monitored and the rate of addition of the alkali solution adjusted so as to maintain pH=12. When the addition was complete, the mixture was allowed to warm to room temperature and stir overnight. The organic layer was removed by siphon and dried with magnesium sulfate for four hours. The mixture was filtered through #4 filter paper on a large Buchner funnel and the sulfate washed with 2*100mL fresh dichloromethane. The combined filtrates were then placed in 2L round bottomed flask and the mixture distilled at torr. Fractions collected from 55 C. to 60 C. were combined and analyzed by NMR. Yield 31.lg (43% based on starting 2-methoxyethylamine). TLC (silica on glass, 2% methanol in dichloromethane) R67 =0.40. 1 H(delta, CDCl3) 3.28(s,3H), 3.40{m,4H}, 3.97{s,2H}, 6.92{br, IH}. 13 C{1 H}{delta, CDCl2 }39.27, 42.32, 58.60, 70.54, 166.22.

According to the analysis of related databases, 109-85-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mallinckrodt Medical, Inc.; US5138040; (1992); A;,
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Reference of 148583-65-7, These common heterocyclic compound, 148583-65-7, name is 4-Fluoro-2-isopropoxyaniline, 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 9 1-(4-Fluoro-2-methylethoxyphenyl)piperazine (XXI) A crude solution of XX (8.35 g, 47.9 mmol), bis-(2-choroethyl)amine hydrochloride (12.83 g, 71.9 mmol) and triethylamine (10.00 mL, 71.7 mmol) in chlorobenzene (70 mL) was heated at reflux for 25 h. The dark brown reaction mixture was then partitioned between 3N NaOH and methylene chloride. The organic layer was separated, dried (MgSO4), filtered and concentrated to yield 15.9 g of a brown oil.

The synthetic route of 148583-65-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; McNeilab, Inc.; US5569659; (1996); A;,
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Related Products of 109-85-3, These common heterocyclic compound, 109-85-3, name is 2-Methoxyethylamine, 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: To a solution of nitrogen-containing nucleophile (1 eq.) and cesium carbonate (3.0 eq.) in N,N-dimethylformamide (2 mL/mmol) was added 2-haloheterocycle (1.1 eq.). Thereaction was heated to 100 C. and stirred at this temperature for 2 hours. Thereaction was then cooled to room temperature and acidified to pH=1 with 10%aqueous HCl solution if product contains a carboxylic acid, or diluted withwater if neutral. The solution was extracted with twice with dichloromethane.The organic layers were combined, dried with sodium sulfate and concentratedunder vacuum. The crude material was either used directly in subsequentreactions or purified by flash chromatography.

The synthetic route of 109-85-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Blaquiere, Nicole; Castanedo, Georgette; Feng, Jianwen A.; Hu, Baihua; Staben, Steven; Yuen, Po-wai; Wu, Guosheng; Lin, Xingyu; Burch, Jason; US2015/57260; (2015); A1;,
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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. 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-2-methoxynaphthalene

In a glove box, 1.0 mmol of 1-bromo-2-methoxynaphthalene, 2.0 mmol of aryl boronic acid, Pd2 (dba) 3, phosphine ligand and 3.0 mmol of potassium phosphate were charged in 7 mL of anhydrous toluene under nitrogen , And the temperature was raised to 80 C, and the reaction was carried out for a period of time. The results are shown in Table 2 below.The amount of Pd2 (dba) 3 and the phosphine ligand is divided into two kinds: (1) 0.25 mol% Pd2 (dba) 3, 0.5 mol% phosphine ligand, or (2) 0.5 mol% Pd2 (dba) mol% phosphine ligand, depending on the amount of ligand used in Table 2.

According to the analysis of related databases, 3401-47-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sun Yat-sen University; Qiu Liqin; Yu Sifan; Zhou Xiantai; (23 pag.)CN106995461; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, 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 31576-51-9, Computed Properties of C5H13NO2

A mixture of 2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2-phenylpropanoic acid (100 mg, 0.2570 mmol) , 2- (2-methoxyethoxy) ethan-1-amine (37 mg, 0.3085 mmol) , HATU (146 mg, 0.3856 mmol) , DIPEA (99 mg, 0.7712 mmol) in DMF (3 mL) was stirred at rt for 3 hours. The reaction mixture was poured into H 2O (10 mL) and extracted with EtOAc (15 mL x 3) . The combined organic layer was washed with brine, dried over Na 2SO 4, concentrated and purified by column chromatography (DCM/MeOH=40: 110: 1) to give the target product (85 mg, 67.48%) . 1HNMR (400 MHz, DMSO-d6) delta 8.24 (s, 1H) , 7.98 (s, 2H) , 7.95 (s, 1H) , 7.56 (t, J = 5.6 Hz, 1H) , 7.34 -7.22 (m, 4H) , 7.15 (dd, J = 7.7, 1.5 Hz, 2H) , 6.74 (dd, J = 3.3, 1.8 Hz, 1H) , 3.46 -3.37 (m, 4H) , 3.29 (dd, J = 5.6, 3.0 Hz, 3H) , 3.22 (dd, J = 13.2, 6.0 Hz, 1H) , 3.13 (s, 3H) , 2.28 (s, 3H) . MS: M/e 491 (M+1) +.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; ZHOU, Changyou; (152 pag.)WO2019/196803; (2019); A1;,
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Application of 2393-23-9, These common heterocyclic compound, 2393-23-9, name is 4-Methoxybenzylamine, 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.

A mixture of l-[4-(methyloxy)phenyl]methanamine (40 g) and 4- (methyloxy)benzaldehyde (40.5 g) in methanol (220 mL) was heated to reflux for 3 hours. After cooling to 0 C, NaBH4 (14.34 g) was added portionwise within 30 min and the resulting mixture was stirred at room temperature overnight. Solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc for 3 times. The combined organic layers were washed with water and brine, then dried over anhydrous Na2SC>4. After filtration, solvent was removed in vacuo to afford bis {[4-(methyloxy)phenyl]methyl} amine (75.9 g) as a colorless oil. MS(ES+) m/z 258 (MH+).

Statistics shows that 4-Methoxybenzylamine is playing an increasingly important role. we look forward to future research findings about 2393-23-9.

Reference:
Patent; GLAXO GROUP LIMITED; WANG, Yonghui; CAI, Wei; LIU, Qian; XIANG, Jia-Ning; WO2012/27965; (2012); A1;,
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