Category: ethers-buliding-blocks

These common heterocyclic compound, 14869-41-1, name is 2-(2-Chloroethoxy)acetic acid, 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. HPLC of Formula: C4H7ClO3

In a glass RBF equipped with a Teflon-coated magnetic stirrer was dissolved (2-chloro-ethoxy)- acetic acid (1 eq.) in dichlormethane (0.67 M). To this was then added sequentially pyridine (2.5 eq.) and thionyl chloride (1.5 eq.), the latter of which was added drop-wise over 10 mm. The resulting orange solution was stirred at RT under nitrogen for 30 mm before 2-bromo-4-fluoro-5- nitro-phenylamine (1 eq.) was added drop-wise as a solution in dichloromethane (0.67 M). Finally, triethylamine (3.5 eq.) and DMAP (0.1 eq.) were added and the resulting mixture was allowed to stir at RT for 18 h. The reaction was quenched with the addition of water and extracted with EtOAc. The combined organic extracts were then washed further with water and brine, dried over MgS 04, filtered and the filtrate concentrated in vacuo. Further purification by way of column chromatography (Si02, gradient elution, 9:1 (v/v) Hex: EtOAc – EtOAc) furnish the desired product as an orange oil that solidified upon standing (51percent yield).

The synthetic route of 2-(2-Chloroethoxy)acetic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; JORAND-LEBRUN, Catherine; LAN, Ruoxi; CHEN, Austin; CLARK, Ryan C.; (268 pag.)WO2017/49068; (2017); 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., Formula: C7H6F3NO

General procedure: To a mixture of substituted phenyl amine (0.06 mol) and 20% HCl (50 mL), NaNO2 (0.123 mol) in H2O (200 mL) was added drop-wise at 0 C. After the completion of addition, the reaction mixture was stirred at this temperature for 30 min, and then it is dropped into the mixture of appropriate intermediate (10a or 10b) (0.047 mol), sodium acetate anhydrous (10.2 g, 0.124 mol), EtOH (200 mL) at 0 C. Upon completing the addition, the mixture was filtered and the cake was dried to give light yellow to white solid (11a-t, 12a and 12b) yielded 75-80%.

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; Li, Sai; Zhao, Yanfang; Wang, Kewen; Gao, Yali; Han, Jianming; Cui, Bingbing; Gong, Ping; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 2843 – 2855;,
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Reference of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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 reaction vessel containing a stirrer, a thermometer and a dropping funnel was charged with 1.36 mol of a 25% sodium sulfite solution, 1.7 mol of a mixture of beta-aminopropanal (2), a mass fraction of 55% Of 2-nitrophenol solution (3) 2.3mol, strontium chloride 0 · 56mol, acetonitrile 300ml, control the stirring speed at 180rpm, raise the temperature of the solution to 135 C, the reaction 9h, static stratification, remove the oil layer , Washed with sodium bromide solution, the mass fraction of 65% isopropyl alcohol, the mass fraction of 75% triethylamine washing, 1.9kPa vacuum distillation, collecting 90-95 C fractions, in the mass fraction of 90% toluene Recrystallization gave 103.43 g of crystalline diethanol acrolein in 83% yield.

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

Reference:
Patent; Chengdu qianyu Longhua Petroleum Engineering Consulting Co. Ltd.; Guan, genan; (5 pag.)CN105503547; (2016); A;,
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Electric Literature of 7252-83-7,Some common heterocyclic compound, 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, molecular formula is C4H9BrO2, 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-bromothiophenol (10.0 g, 52.88 mmol) in DMF (180 mL) was added NaH (3.0 g, 63.45 mmol) portionwise at 0C. After the addition, the reaction mixture was stirred at room temperature for 30 mi Bromoacetaldehyde dimethylacetal (6.85 mL, 58.17 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with EtOAc (250 mL) and washed with cold water and brine solution. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford the crude material which was purified by column chromatography using silica gel (100-200 mesh) and 2% EtOAc-hexane as eluent to afford 1-bromo-3-(2,2-dimethoxy- ethylsulphanyl)-benzene (11.0 g, 36.038 mmol, 68%) as colorless liquid. GCMS: 277 (mlz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1,1-dimethoxyethane, its application will become more common.

Reference:
Patent; CURADEV PHARMA PRIVATE LTD.; BANERJEE, Monali; MIDDYA, Sandip; SHRIVASTAVA, Ritesh; RAINA, Sushil; SURYA, Arjun; YADAV, Dharmendra B.; YADAV, Veejendra K.; KAPOOR, Kamal Kishore; VENKATESAN, Aranapakam; SMITH, Roger A.; THOMPSON, Scott K.; WO2014/186035; (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. 1663-61-2, name is (Triethoxymethyl)benzene, A new synthetic method of this compound is introduced below., Quality Control of (Triethoxymethyl)benzene

2-Azido-3-hydroxypropyl benzoate (27): Neat 23 (1.48 g, 12.65 mmol) was dissolved in CH2Cl2 (127 mL) and treated with a catalytic amount of p-toluene sulfonic acid monohydrate (0.048 g, 20 mumol) and (trimethoxymethyl)benzene (3.26 mL, 18.98 mmol) in CH2Cl2 at room temperature for 1 hr. After the formation of the orthoester was complete, a stoichiometric amount of water (340 muL, 18.98 mmol) was added to the mixture. The mixture was then stirred for 40 min and concentrated in vacuo. Purification of the residue by silica gel flash chromatography using 25percent EtOAc/hexanes gave 2.6 g of monoacylated product 27 (93percent yield) as a clear, colorless oil. 1H NMR (CDCl3, 400 MHz) delta: 8.03-8.06 (m, 2H), 7.58 (tt, J=1.6, 2.0, 1.6 1H), 7.43-7.47 (m, 2H), 4.54 (dd, J=4.4, 12.0 Hz, 1H), 4.46 (dd, J=6.8, 12.0 Hz, 1 H), 3.85-3.91 (m, 1H), 3.80 (dd, J=4.8, 11.6 Hz, 1H), 3.73 (dd, J=6.0, 11.6 Hz, 1H).

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; SIEMENS MEDICAL SOLUTIONS USA, INC.; US2009/10846; (2009); A1;,
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Electric Literature of 450-91-9, These common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-methoxyaniline, 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.

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (15.0 g), 4-fluoro-2-methoxyaniline (9.5 g), 4M hydrochloric acid in dioxane (4.5 ml) and dioxane (100.0 ml) were stirred at 100 C. overnight. Then the mixture was filtrated and the solid was dried in vacuo. Yield: 24.0 g ESI mass spectrum: m/z=348 (M+H)+

The synthetic route of 450-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/212103; (2011); A1;,
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Synthetic Route of 70894-71-2, A common heterocyclic compound, 70894-71-2, name is N-(4-Methoxybenzyl)cyclopropanamine, molecular formula is C11H15NO, 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.

6-Chloro-8-(cyclopropyl(4-methoxybenzyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile To a stirred solution of 6,8-dichloroimidazo[1,2-b]pyridazine-3-carbonitrile and 8-bromo-6-chloroimidazo[1,2-b]pyridazine-3-carbonitrile (15 g, 71.09 mmol) in THF (20 mL) was added DIPEA (14 mL, 78.19 mmol) at room temperature under argon atmosphere, prior to the addition of N-(4-methoxybenzyl)cyclopropanamine (13.99 g, 78.19 mmol) at room temperature. The reaction mixture was stirred for 4 h at 65 C. The reaction mixture was quenched with water and extracted with ethyl acetate (2*200 mL). The combined extracts were washed with brine, dried over Na2SO4, concentrated to give the crude product, which was purified on a silica gel column (eluting with 20% ethyl acetate: pet ether) to get the title compound 6-chloro-8-(cyclopropyl(4-methoxybenzyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile (18 g, 71.1%) as a pale yellow solid. ES+, m/z 354.4 [M+1].

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; Polaris Pharmaceuticals; WEBBER, Stephen E.; TAO, Xueliang; BRIN, Elena; (85 pag.)US2017/369489; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 80936-82-9, name is 4-(Methoxymethyl)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 80936-82-9, Recommanded Product: 4-(Methoxymethyl)aniline

Example 2 4-amino-7-(tert-butyl)-N-(4-(methoxymethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide 2.43 g of HATU was added to a solution of 1.00 g of 4-amino-7-(tert-butyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid obtained in step 5 of Reference Example 5, 878 mg of 4-(methoxymethyl)aniline, and 2.23 mL of N,N-diisopropylethylamine in 20 mL of DMF at room temperature. The mixture was stirred at room temperature overnight, and an aqueous sodium hydroxide solution was added thereto, followed by extraction with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel chromatography. After concentration, the obtained precipitate was suspended and washed with methanol, followed by filtration and drying under reduced pressure, thereby obtaining 1.12 g of the title compound.

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-(Methoxymethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; MIYAZAKI, Isao; SHIMAMURA, Tadashi; KATO, Masanori; FUJITA, Hidenori; IGUCHI, Satoru; (161 pag.)US2018/9818; (2018); A1;,
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Reference of 60789-54-0,Some common heterocyclic compound, 60789-54-0, name is ((4-Bromobutoxy)methyl)benzene, molecular formula is C11H15BrO, 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.

Reference Example 32 3-(4-Benzyloxybutoxy)-4-(morpholin-4-yl)benzaldehyde 3-Hydroxy-4-(morpholin-4-yl)benzaldehyde (0.28g) and potassium carbonate (0.38g) were suspended in N,N-dimethylformamide (2 mL). To the reaction mixture was added benzyl 4-bromobutylether (0.36g), and the mixture was stirred at 50C for 16 hours. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesiumsulfate. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/5) to give the title compound (0.50g). 1H―NMR (CDCl3) delta ppm:

The synthetic route of 60789-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP1698635; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7664-66-6, name is 4-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 7664-66-6, Recommanded Product: 7664-66-6

The 234 mg (1mmol) 4 – iodo anisole, 465 mg (5mmol) aniline, 38 mg (0.2mmol) CuI, 116.4 mg (0.4mmol) ligand L14, 20mg (0.5mmol) NaOH, 2mL1, 5 – pentanediol, adding 10 ml reaction tube, sealing, 80 C reaction under the condition of 50h. After the stop of the reaction, water, extracted with ethyl acetate, washing, saturated salt water washing, after drying with anhydrous sodium sulfate, filtered, the filtrate is distilled under reduced pressure, purification by silica gel chromatography separation column column, N – 2, 4 – dimethyl shall phenylaniline 244 mg, yield 95%.

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; Sun Yat-sen University; Wan Yiqian; Ding Xiaomei; Huang Manna; Zhu Xinhai; Yi Zhou; CN106883132; (2017); A;,
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