Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 22236-10-8, name is 4-(Difluoromethoxy)aniline, 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 22236-10-8, Formula: C7H7F2NO

Example 2 3- { [4- (DIFLUOROMETHOXY) PHENYL] AMINO}-1- (2-METHOXYETHYL)-4-PHENYL-LH-PYRROLE-2, 5- dione 3-CHLORO-1-(2-METHOXYETHYL)-4-PHENYL-LH-PYRROLE-2, 5-dione (0.13 mmol, 36 mg) AND 4- difluoromethoxyaniline (0.28 mmol, 45 mg) were dissolved in DMF (1 mL). The mixture was heated in a microwave reactor at 150C for 20 min.. After cooling, the reaction mixture was purified by HPLC (95% 0. 1M ammonium acetate buffer: 5% CH3CN No. 100% CH3CN) to give 13 mg (24%) of the title COMPOUND. 1H NMR (400 MHz, CDC13) : 8 7.25 (bs, 1H), 7.19-7. 08 (m, 3H), 7.02-6. 97 (m, 2H), 6.81-6. 75 (m, 2H), 6.66-6. 60 (m, 2H), 6.36 (t, J=74.0 Hz, 1H), 3. 83 (t, J=5.7 Hz, 2H), 3.63 (t, J=5.7 Hz, 2H), 3. 38 (s, 3H)

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

Reference:
Patent; ASTRAZENECA AB; WO2005/5417; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 454-90-0, name is 3-(Trifluoromethyl)anisole, 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 454-90-0, Quality Control of 3-(Trifluoromethyl)anisole

In each of the examples in Table 3A, the substrate is reacted with the base in THF to form a metallic organoborate intermediate under the temperature and time conditions specified in Table 3A. The metallic organoborate intermediate is then reacted with the electrophile, E, in THF to form the functionalized products 11b to 11g under the following conditions:Similarly, the substituted arenes 10b-d reacted with 2b (25 C, 0.5-12 h) affording the corresponding borate which lead after subsequent cross-coupling (ZnCl2 (10 mol%), Pd(OAc)2 (3 mol%), S-Phos (6 mol%), 65 C, 1 h) with 12 (0.8 equiv) to the biphenyl derivatives llb-d in 75-95% yield (Table 3A, entries 2-4). For example, tmpBEtyMgCl LiCl (2.2 mL, 1.0 M in THF, 2.2 mmol) was added dropwise at 25 C to a solution of 3,5-(trifluoromethyl)anisole (10b; 352 mg, 2.0 mmol) in THF (2 mL) in a flame-dried and Argon-flushed Schlenk-tube equipped with septum and magnetic stirring bar. After stirring for 1 h at 25 C, ZnCl2 (0.2 mL, 1 M in THF, 10 mol%), Pd(OAc)2 (14 mg, 3 mol%), S-Phos (25 mg, 6 mol%) and ethyl 4-iodobenzoate (12; 441 mg, 1.6 mmol) were added followed by continuously stirring for 1 h at 65 C. After cooling to 25 C, the reaction mixture was diluted with Epsilon2Omicron (5 mL) and quenched with sat. NH4C1 (aq.) (5 mL). The aqueous layer was extracted with CH2CI2 (3x 15 mL). The combined organic phases were dried over Na2SC>4 and the solvent was removed under vacuum. Flash column chromatography (pentane-Et20, 9: 1) afforded lib (492 mg, 95%) as a pale yellow solid.

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; HAAG, Benjamin; WO2012/85169; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C13H14ClNO

4-{[4-(Benzyloxy)phenyI]amino}-2-tert-butyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide; 2-fert-Butyl-4-chloro-5~phenylisothiazol-3(2H)-one 1,1-dioxide (0.3g, 1 mmol), 4- benzyloxyaniline hydrochloride (0.307g, 1.3 mmol) and TEA (0.304g, 3 mmol) was dissolved in dry DMSO (10 ml). The reaction was heated at 110 C for 25 min in a microwave reactor. The reaction mixture was diluted with water (200 ml) and extracted with EtOAc (200 ml), the organic phase was dried (MgSO4), filtered and evaporated. The residue was purified by silica gel column chromatography using a 65:35 mixture of heptane:EtOAc as eluant to give the title compound (0.345 g, 75 %).

The synthetic route of 51388-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2006/73363; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 22483-09-6, These common heterocyclic compound, 22483-09-6, name is 2,2-Dimethoxyethanamine, 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.

100 g of aminoacetaldehyde dimethyl acetal and 146 g of benzaldehyde are added to 2.5 liters of toluene, heated to reflux for 16 hours, and concentrated.The residue was dissolved in 1.8 L of methanol, 45 g of sodium borohydride was slowly added in portions, and the mixture was stirred at room temperature for 5 hours.Saturated ammonium chloride solution was added and extracted with ethyl acetate, followed by liquid separation, drying,Concentration gave 162 g of N-benzyl-2,2-dimethoxyethanamine and the crude product was used in the next reaction without purification.

Statistics shows that 2,2-Dimethoxyethanamine is playing an increasingly important role. we look forward to future research findings about 22483-09-6.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Bu Gonggaofamingren; (6 pag.)CN107778208; (2018); A;,
Ether – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, 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 60792-79-2, name: 2,2′-Oxybis(ethylamine) dihydrochloride

To a solution of 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (0.55 g, 1.95 mmol) in 1-methyl-2-pyrrolidone (40 mL) bis-(2-aminoethyl)-ether dihydrochloride (2.1 g, 11.9 mmol, 6eq.) and DBU (3.49 mL, 23.4 mmol, 12 eq.) added and the reaction mixture was stirred at 110 C. for 18 hours. The reaction mixture was then diluted with water (70 mL) and the pH was adjusted to 11 and extracted with CH2Cl2 (9*40 mL). Water layer was then acified with H2SO4 to pH 6.8, extracted with 50 mL of CH2Cl2 and then evaporated in vacuum. Crude product was diluted in 2-propanol (60 mL), stirred at 82 C. for 20 minutes and filtrated. Precipitate was pure salt (Na2SO4). 2-Propanol was evaporated in vacuum and product was purified by column chromatography (fraction, eluent: CH2Cl2-MeOH-NH3-CH3CN=4:4:2:1) yielding 0.5 g of title compounds as a mixture of chloro and fluoro derivatives in ratio 3:1 MS (ES+) m/z: [MH]+=365.8 (A) (75%) MS (ES+) m/z: [MH]+=349.4 (B) (25%).

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; Pliva-Istrazivacki Institut d.o.o.; Glaxo Group Limited; US2006/258600; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 162705-07-9, 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 162705-07-9 as follows.

General procedure: DCC (0.47 mmol, 1.2 eq.); the N-Fmoc-protected amino acid (0.472 mmol, 1.2 eq) and HOBt·H2O (0.47 mmol, 1.2 eq) were added to a solution of the 30-aminocombretastatin (0.39 mmol, 1 eq) in anhydrous DMF (1.3 mL). The reaction mixture was stirred under N2 atmosphere for 16 h. Then, it was ltered, and the ltrate was poured into a saturated aqueous NH4Cl solution and then extracted with AcOEt (3×15 mL). The combined organic extracts were washed 2 times with water and brine and dried over anhydrous MgSO4. After ltration and evaporation of the solvent under reduced pressure, the resulting residue was chromatographed on silica gel with Hexanes-AcOEt (6:4) to aord the corresponding N-Fmoc-protected derivatives 7 and 9.

According to the analysis of related databases, 162705-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Agut, Rauel; Alberto Marco, J.; Carda, Miguel; Falomir, Eva; Gil-Edo, Raquel; Martin-Beltran, Celia; Murga, Juan; Pla, Alberto; Molecules; vol. 25; 3; (2020);,
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Synthetic Route of 2062-98-8, A common heterocyclic compound, 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, molecular formula is C6F12O2, 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.

In an argon atmosphere, put 0.50 g (4.2 mmol) of 4-hydroxystyrene into a three-necked flask, add 20 mL of dichloromethane, and add 1.99 g (6 mmol) of hexafluoropropylene oxide di containing acid fluoride end groups while stirring. Polymer (CF3CF2CF2OCF (CF3) COF, provided by Zhejiang Huanxin Fluoro Material Co., Ltd., recorded as FEOCOF), after the addition, 0.05 mL (0.0007 mmol) DMF was added, and 0.4 mL (0.003 mmol) of dry After triethylamine was added dropwise, the reaction was stirred at 40 C for 4h. After the reaction, 20 mL of deionized water was added and extracted with dichloromethane (20 mL × 3). The organic phases were combined and dried over MgSO 4, filtered, and rotary evaporated to obtain a crude product. The crude product was separated by silica gel column chromatography (washed with petroleum ether). Remover) to obtain a colorless slightly viscous liquid, the target product, with a yield of 99.5%

The synthetic route of 2062-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaanxi Normal University; Yang Le; Chen Jiangang; Liu Zhaotie; Zhang Qiyu; Li Ruiqing; Shen Shukun; Liu Zhongwen; (11 pag.)CN110776426; (2020); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 7664-66-6, The chemical industry reduces the impact on the environment during synthesis 7664-66-6, name is 4-Isopropoxyaniline, I believe this compound will play a more active role in future production and life.

4-Isopropoxy-phenylamine (1.52 g, 10 mmol) in CH2Cl2 (10 mL) was slowly added to 1,1′-carbonyldiimidazole (CDI, 1.64 g, 10 mmol) in CH2Cl2 (5 mL) at 0 C. After stirring at room temperature for 1 h, 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2.05 g, 10 mmol) in CH2Cl2 (5 mL) was added and the mixture was kept stirring at room temperature overnight. It was quenched with water and extracted with CH2Cl2. The organic extracts were washed with brine, dried over Na2SO4 and evaporated. A portion of the BOC-protected product (0.35 g, 0.93 mmol) was re-dissolved in CH2Cl2 (5 mL). To this solution was added 1 mL of trifluoroacetic acid and the resulting mixture was stirred at room temperature for 1 h. The organic solvents were removed in vacuo and the crude material was neutralized with 2 M NH3 in MeOH. After evaporation of the solvents, the crude residue was purified by flash column chromatography on silica gel (5% MeOH/CH2Cl2) to afford the product as a light brown solid (250 mg, 97%). 1H NMR (CDCl3) delta 7.26 (m, 2H), 6.84 (d, J=8.70 Hz, 2H), 6.49 (br, 1H), 4.88 (m, 1H), 4.48 (sep, J=6.0 Hz, 1H), 3.12 (m, 2H), 2.83 (m, 2H), 2.04 (m, 2H), 1.71 (m, 2H), 1.31 (d, J=6.0 Hz, 6H); LC/MS (ESI) calcd for C15H23N2O3 (MH)+ 279.2, found 279.3.

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-Isopropoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Baumann, Christian Andrew; Gaul, Michael David; US2006/281700; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 3616-56-6, 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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, This compound has unique chemical properties. The synthetic route is as follows.

Step 8B: Compound 8-2; To a flask containing (R)-1-{4-[2-((S)-l-amino-2-methyl-propyl)-6-fluoro-phenyl]- piperazin-l-yl}-3- (4-chloro-phenyl)-2-methyl-propan-l-one (43 mg, 0. 10 mmol) and (2,2- diethoxy-ethyl) -dimethyl-amine (100 pL, 0.50 mmol), TFA (30011L, 4.0 mmol) was added via syringe. After-5 min. , NaCNBH3 (95 mg, 1.5 mmol) was added and the resulting mixture was heated to 120 °C overnight. The resulting brown reaction mixture was concentrated in vacuo and purified via preparative HPLC/MS to furnish 8-2 (3.8 mg, 0.006 mmol, 6percent) as the TFA salt. LCMS-tR (method 4) 1.596 min. m/z 502.8 (M+ + H+).

The chemical industry reduces the impact on the environment during synthesis 2,2-Diethoxy-N,N-dimethylethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2005/42516; (2005); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 39538-68-6, 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 39538-68-6 as follows.

To a solution of 3a (550 mg,4 mmol) in 3 mL concentrated HCl at 0 C was added NaNO2(320 mg, 4.6 mmol; dissolved in 5 mL H2O), and the mixture was stirred at 0 C for 1 h. A solution of KI (950 mg, 5.7 mmol; dissolvedin 10 mL H2O) was added dropwise at 0 C, and the mixture was slowly warmed up to room temperature overnight with stirring. The mixture was extracted with ether and the combined organic layers were washed with brine, dried over anhydrous MgSO4, and evaporated under reduced pressure. The residue was purified by silica gel flash chromatography (hexane as eluent) to give the titled product as colorless oil (0.826 g, 84% yield): 1H NMR (400 MHz, CDCl3) delta 7.62 (d, J=7.9 Hz, 1H), 6.65 (s, 1H), 6.55 (d, J=7.9 Hz, 1H), 3.87 (s, 3H), 2.33 (s, 3H).

According to the analysis of related databases, 39538-68-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Muppidi, Avinash; Doi, Kenichiro; Ramil, Carlo P.; Wang, Hong-Gang; Lin, Qing; Tetrahedron; vol. 70; 42; (2014); p. 7740 – 7745;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem