Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 54314-84-0, name is ((3-Bromopropoxy)methyl)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 54314-84-0, COA of Formula: C10H13BrO

(Step 3) {1-[1-(1-Tert-butyloxycarbonyl)piperidin-4-yl] imidazolidin-2-ylidene}malononitrile (3.68 g, 11.59 mmol) obtained in the Step 2 was dissolved in DMF (25 mL) and the solution was added with potassium carbonate (3.20 g, 23.18 mmol) and benzyl-3-bromopropylether (2.46 mL, 13.91 mmol), followed by stirring at 80°C for 6.5 hours. Further, the mixture was added with potassium carbonate (1.60 g, 11.59 mmol) and benzyl-3-bromopropylether (1.72 mL, 5.80 mmol), followed by stirring at 80°C for 14.5 hours. The mixture was added with saturated brine and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol (20:1)) to obtain {3-(3-benzyloxypropyl)-1-[1-(1-tert-butyloxycarbonyl)piperidin-4-yl]imidazolidin-2-ylidene} malononitrile (4.84 g, 89.6 percent) as a white solid. 1H NMR (CDCl3, deltappm): 1.45 (s, 9H), 1.49-1.56 (m, 2H), 1.74-1.79 (m, 2H), 1.94-2.04 (m, 2H), 2.81 (brt, J = 12.3 Hz, 2H), 3.38-3.45 (m, 2H), 3.52-3.60 (m, 4H), 3.69 (t, J = 7.1 Hz, 2H), 4.18-4.35 (m, 3H), 4.49 (s, 2H), 7.26-7.38 (m, 5H).

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, ((3-Bromopropoxy)methyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1847530; (2007); A1;,
Ether – Wikipedia,
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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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-(4-Methoxyphenyl)ethylamine

To a solution of [3-(3,5-Dimethoxy-phenyl)-1 ,4-dimethyl-1 H-pyrazolo[3,4-b]pyridin-6-yloxy]- acetic acid (building block A1 , 100 mg, 0.28 mmol) in CH2CI2 were added HOBt x H20 (64 mg, 0.42 mmol), EDC x HCI (80 mg, 0.42 mmol) and NEt3 (0.12 ml, 0.84 mmol). After stirring at rt for 5 min, (S)-1-(4-methoxyphenyl)ethanamine (64 mg, 0.42 mmol) was added andstirring continued for 18 h. Then, water was added and the mixture extracted 3 times withDCM. The organic phases were dried over Na2S04 and the solvent removed under reduced pressure. Purification by reverse phase HPLC (Sunfire C18 OBD column) followed byliberation of the free base (SPE cartridge SCX-1 , eluent 7M NH3 in methanol) yielded the title compound (17 mg, 12%). [1 H-NMR (DMSO-d6, 600 MHz) delta 8.48 (d, 1 H), 7.21 (d, 2H),6.82 (d, 2H), 6.70 (s, 1 H), 6.58 (s, 1 H), 5.00-4.88 (m, 1 H), 4.87 (d, 1 H), 4.83 (d, 1 H), 3.85 (s, 3H), 3.78 (s, 6H), 3.70 (s, 3H), 2.37 (s, 3H), 1.37 (d, 3H); UPLC-MS Rtj = 1.14 min; [M+H]+ = 491.2]

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; NOVARTIS AG; BADIGER, Sangamesch; BEHNKE, Dirk; BETSCHART, Claudia; CHAUDHARI, Vinod; CHEBROLU, Murali; COSTESTA, Simona; HINTERMANN, Samuel; MEYER, Arndt; PANDIT, Chetan; WO2011/76744; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35822-58-3, name is 2-Bromobenzaldehyde diethyl acetal, 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 35822-58-3, Formula: C11H15BrO2

To a solution of aryl bromide (1.94 g, 7.49 mmol, 1.0 equiv) in THF (20 mL) at -78 C under N2 was added 1.5 M n-BuLi in hexanes (7.49 mL, 11.2 mmol, 1.5 equiv). After 30 mm DMF (869 iL, 11.2 mmol, 1.5 equiv) was added. The mixture was slowly warmed to r.t. over 4 h, at which time it was quenched with sat. aq. NH4C1 (40 mL) and extracted with EtOAc (3 x 20 mL). The organics were dried over Na2SO4, filtered and concentrated in vacuo. The resultant oil was purified by flash chromatography on silica gel (95:4:1 hexanes/EtOAc/Et3N) to yield the product (2.105 g, 87%) as a yellow oil. R1= 0.46 (3:1 hexanes/EtOAc). The analytical data match those previously reported: Ueda, M.; Kawai, S.; Hayashi, M.; Naito, T.; Miyata., 0. 1 Org. Chem. 2010, 75, 914.

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; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; SALK INSTITUTE FOR BIOLOGICAL STUDIES; PACHE, Lars; CHANDA, Sumit, K.; VAMOS, Mitchell, Dennis; COSFORD, Nicholas David, Peter; TERIETE, Peter; MARLETT, John; DIAZ, Arturo; YOUNG, John, A.T.; WO2015/187998; (2015); A2;,
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Application of 6298-96-0, 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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 6.1(S)-2-((3-(3,5-dimethoxyphenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)oxy)-N-(1-(4-methoxyphenyl)ethyl)acetamide To a solution of [3-(3,5-Dimethoxy-phenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yloxy]-acetic acid (building block A1, 100 mg, 0.28 mmol) in CH2Cl2 were added HOBt×H2O (64 mg, 0.42 mmol), EDC×HCl (80 mg, 0.42 mmol) and NEt3 (0.12 ml, 0.84 mmol). After stirring at rt for 5 min, (S)-1-(4-methoxyphenyl)ethanamine (64 mg, 0.42 mmol) was added and stirring continued for 18 h. Then, water was added and the mixture extracted 3 times with DCM. The organic phases were dried over Na2SO4 and the solvent removed under reduced pressure. Purification by reverse phase HPLC (Sunfire C18 OBD column) followed by liberation of the free base (SPE cartridge SCX-1, eluent 7M NH3 in methanol) yielded the title compound (17 mg, 12%). [1H-NMR (DMSO-d6, 600 MHz) delta 8.48 (d, 1H), 7.21 (d, 2H), 6.82 (d, 2H), 6.70 (s, 1H), 6.58 (s, 1H), 5.00-4.88 (m, 1H), 4.87 (d, 1H), 4.83 (d, 1H), 3.85 (s, 3H), 3.78 (s, 6H), 3.70 (s, 3H), 2.37 (s, 3H), 1.37 (d, 3H); UPLC-MS RtJ=1.14 min; [M+H]+=491.2]

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, 1-(4-Methoxyphenyl)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; US2012/258973; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 171290-52-1, 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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 2 (0.50 g, 1.40 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.05 g, 0.07 mmol), copper(I) iodide (0.03 g,0.14 mmol), triphenylphosphine (0.02 g, 0.08 mmol) and triethylamine(0.17 g, 1.68 mmol) in 4:1 DMF-water (v/v, 20 mL) was placed in a two necked round-bottomed flask equipped with a stirrer bar, condenser and a rubber septum. The mixture was flushed with argon gas for30 min and a solution of phenylacetylene derivative (1.2 equiv.) in DMF(2 mL) was introduced via a rubber septum by means of a syringe. A balloon filled with argon was connected to the top of the condenser andthe mixture was left to stir at 70 C for 2 h. The mixture was allowed to cool and then poured into crushed ice. The product was extracted into chloroform and the combined organic phases were washed with water and dried over anhydrous MgSO4. The salt was filtered off and the solvent was evaporated under reduced pressure on a rotary evaporator.The residue was purified by column chromatography on using silica gelusing 9:1 toluene-ethyl acetate mixture (v/v) as an eluent. The following compounds were prepared in this fashion.

The chemical industry reduces the impact on the environment during synthesis 3,5-Dimethoxyphenylacetylene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Olomola, Temitope O.; Mphahlele, Malose J.; Journal of Fluorine Chemistry; vol. 229; (2020);,
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Application of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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.

Tert-butyl 2-acetyl-3 – ((tert-butyldimethylsilyl) oxy) -5- (methoxymethyloxy) -6- (pivaloyloxy) benzoate (5.00 g, 9.79 mmol, 1 eq) 0 g), and the temperature was raised to 85 C. Subsequently, N, N-dimethylformamide-di-tert-butylacetal (1.99 g, 9.79 mmol, 1 eq) was added thereto, followed by stirring at 85 C. After stirring for 2.5 hours, it was cooled to room temperature and concentrated under reduced pressure to remove half of the solvent amount (25.0 g). The same amount of toluene as the distilled solvent was added and heated again to 85 C. Then N, N-dimethylformamide-di-tert-butylacetal (1.99 g, 9.79 mmol, 1 eq) was added and the mixture was incubated for 2 hours did. The reaction solution was concentrated under reduced pressure until the solvent disappeared, toluene was added to this concentrated solution, the total amount was adjusted to be 20 times by weight of the product on the assumption that the yield was 100%. Iodine (2.02 g, 7.96 mmol, 3 eq) and pyridine (0.21 g, 2.65 mmol, 1 eq) were added to 30.0 g of the adjusted solution (estimated to contain 1.50 g of enamine compound, 2.65 mmol) C. for 2 hours. Acetic acid (0.30 mL, 5.30 mmol, 2 eq) was added after confirming the disappearance of the raw material by HPLC analysis, and after reacting at 50 C. for 3 hours and 30 minutes, 15% aqueous sodium thiosulfate solution (26.7 g) Was added and stirred, and the organic phase was taken out. The organic phase was washed with water (7.5 g) and concentrated under reduced pressure. Toluene was added to the obtained crude product, and the total amount was adjusted to 5.2 g. Heptane (7.0 g) was added to the solution, and the mixture was cooled to 5 C. and recrystallized to obtain tert-butyl 3-iodo-7- (methoxymethyloxy) -4-oxo-6- (pivaloyloxy) -4H- Chromene-5-carboxylate as a white solid (yield 72.3%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its application will become more common.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; Tanaka, Yui; Fujiwara, Yuji; (25 pag.)JP2015/113324; (2015); A;,
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Application of 111-95-5, 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 111-95-5 as follows.

EXAMPLE 17 Bis-(2-methoxy-ethyl)-prop-2-ynyl-amine Propargyl bromide (17.8 g, 150 mmol) was added dropwise to a mixture of bis(2-methoxy-ethyl)amine (20 g, 150 mmol) and cesium carbonate (49 g, 150 mmol) in 350 mL of acetone. The mixture was stirred overnight under nitrogen at room temperature. The inorganic salts were then filtered off, and the solvent was removed. The residue was dissolved in saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic extracts were then evaporated to give 20 g of bis-(2-methoxy-ethyl)-prop-2-ynyl-amine: mass spectrum (m/e): M+H 172.

According to the analysis of related databases, 111-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Cyanamid Company; US6288082; (2001); B1;,
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Ether | (C2H5)2O – PubChem

Reference of 175278-17-8, A common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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: Tert-butyl (R)-(5-(trimethylsilyl)pent-4-yn-2-yl)carbamate (160 mg, 0.63 mmol) was added in DMF (2.5 mL) to a sealed vial containing amino-halide (0.5 mmol), sodium carbonate (106 mg, 1.00 mmol), lithium chloride (21.00 mg, 0.50 mmol) and Pd(dppf)Cl2.CH2Cl2 (14.62 mg, 0.02 mmol). The reaction was degassed for 10 min, then heated to 100 C for 4 hours. After cooling, the reaction was diluted with EtOAc and washed with water and brine. The organic was dried over Na2SO4 and evaporated, then the crude product was purified by flash silica chromatography (EtOAc / heptane). Pure fractions were evaporated to dryness to afford the indole.

The synthetic route of 175278-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moss, Thomas A.; Lister, Andrew S.; Wang, Jimmy; Tetrahedron Letters; vol. 58; 32; (2017); p. 3136 – 3138;,
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Application of 592-55-2, A common heterocyclic compound, 592-55-2, name is 1-Bromo-2-ethoxyethane, molecular formula is C4H9BrO, 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 stirred solution of 3-hydroxybenzaldehyde 1 (15 g, 122.9 mmol) in DMSO (100 mL) and 10 % aqueous NaOH solution was added 1-bromo-2-ethoxyethane 2 (34 mL, 307.3 mmol) in DMSO (50 mL) drop wise at 80 C then stirred at same temperature for 10 h. After completion of reaction as indicated by TLC, reaction mixture was poured into 1M HCl solution (200 ml) and extracted with diethyl ether (2x 500 mL). Combined organic layers were washed with brine solution (100 mL), dried over Na2SO4 and concentrated under reduced pressure to afford 3-(2-ethoxyethoxy) benzaldehyde 3 (5.4 g, 27.83 mmol, 22 %) as a colorless oily liquid. TLC system: 30 % ethyl acetate in pet ether – Rf: 0.50; LCMS: m/z = 195.31 (M+H) +

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; COCRYSTAL PHARMA, INC.; JACOBSON, Irina, C.; LEE, Sam SK; FEESE, Michael, David; (206 pag.)WO2020/23813; (2020); 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. 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H9BrO2

To a mixture ofl-bromo-2,4-dimethoxybenzene (72 jiL, 0.50 mmol, 1 equiv), cyclopropylboronic acid (64 mg, 0.75 mmol, 1.5 equiv), and K3PO4H2O (0.35 mg, 1.5 mmol, 3 equiv) was added toluene (400 iL) then a THF stock solution of 3 and PAd3 (100 iL, 0.25 iimol of Pd/PAd3) and the mixture was stirred at 100 C for 5 h. The reaction mixture was diluted withethyl acetate then extracted with water. The combine organic layers were evaporated and the crude product was purified by flash chromatography. After drying, 80 mg (90 %) of 23 was obtained as a colorless oil. NMR spectroscopic data agreed with literature values.

According to the analysis of related databases, 17715-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE TRUSTEES OF PRINCETON UNIVERSITY; CARROW, Brad P.; CHEN, Liye; (51 pag.)WO2017/75581; (2017); A1;,
Ether – Wikipedia,
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