Month: May 2021

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 33839-11-1 as follows. category: ethers-buliding-blocks

3-EthyI-4-methoxyphenylboronic acid 6. To a stirred solution of 4-bromo-2-ethyl-l-methoxybenzene (4.59 g, 21 mmol) in dry THF (50 mL)5 cooled to -78C5 was added slowly drop-wise (over 45 min) n-BuLi (15 mL of a 1.6 M solution in hexanes, 24 mmol). The solution was stirred at -78C for 2 h before trimethylborate (3.6 mL, 31.5 mmol) was added drop-wise and the reaction was allowed to warm slowly to rt with stirring overnight. The reaction was quenched with 2M HCl (50 mL) and the products extracted with EtOAc (2 x 50 mL). These extracts were combined and concentrated under reduced pressure to give an oily substance. To this was added hexane followed by a small amount of DCM and the resulting white precipitate was collected by filtration and washed with hexane. Yield 1.55 g, 41%: 1H NMR delta (270 MHz, CDCl3) 1.27 (3H, t, J= 7.5 Hz)5 2.73 (2H5 q, J = 7.5 Hz)5 3.90 (3H5 s), 6.60 (-1H5 bs), 6.96 (IH5 d, J = 8.4 Hz)5 7.98 (IH5 d5 J = 1.5 Hz)5 8.08 (IH5 dd, J = 8.2, 1.7 Hz); LC/MS (APCI) m/z 179.04 (M-H)”; HPLC ttau = 2.1 min (>99%) 90% MeCN in H2O.

According to the analysis of related databases, 33839-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; STERIX LIMITED; WO2007/96647; (2007); A2;,
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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. 131713-50-3, name is 2,2-Dimethoxypropan-1-amine, A new synthetic method of this compound is introduced below., SDS of cas: 131713-50-3

Step 1 A solution of Cbz-D-Valine (500 g, 1.99 mol) and N-methylmorpholine (201.8 g, 1.99 mol) in anhydrous THF (8 L) was cooled to -15 C., i-butylchlorofomate (299 g, 2.19 mol) was added dropwise under stirring. After 30 min, a solution of 1-amino-2,2-dimethoxypropane (209.5 g, 1.99 mol) in THF (1 L) was added slowly and the temperature was maintained at -15 C. for 2 h. The reaction mixture was washed with brine (2 L) and the organic phase was concentrated to remove the THF. The residue was diluted with EtOAc (4 L), washed with 1N aqueous HCl (2*2 L), washed with sat. NaHCO3 (2 L) and Na2CO3 (2 L), and washed with brine (1.5 L). After drying over Na2SO4, the organic solvent was removed under reduce pressure to afford (R)-benzyl (1-((2,2-dimethoxyethyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate as a white solid (670 g, yield 99.5%), which was used for next step without further purification. LC-MS m/z 360.9 [M+Na]+. 1H NMR (CD3OD 300 MHz): delta 7.35-7.30 (m, 5H), 5.08 (s, 2H), 4.45-4.35 (m, 1H), 3.95-3.85 (m, 1H), 3.34-3.25 (m, 8H), 2.10-1.90 (m, 1H), 0.94-0.91 (m, 6H).

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; Vitae Pharmaceuticals, Inc.; Gregg, Richard E.; US2015/250787; (2015); A1;,
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Related Products of 1000574-79-7, A common heterocyclic compound, 1000574-79-7, name is 2-Bromo-4-(difluoromethoxy)aniline, molecular formula is C7H6BrF2NO, 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.

(25a) N-[2-Bromo-4-(difluoromethoxy)phenyl]formamide Into acetonitrile (80 mL), 2-bromo-4-(difluoromethoxy)aniline (4.40 g, 18.5 mmol) and formic acid (1.1 mL, 27.5 mmol) were dissolved, to which 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (7.7 g, 28 mmol) and 4-methylmorpholine (3 mL, 27 mmol) were added, followed by stirring at room temperature for six hours. Ethyl acetate and water were added for extraction, and the resulting organic layer was sequentially washed with water and saturated brine and then dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue thus obtained was purified by silica gel column chromatography (hexane : ethyl acetate, 100 : 0 – 60 : 40, V/V) to give the desired title compound (4.1 g, yield 83%). 1H-NMR (CDCl3) 5: 6.47 (1H, t, J = 73.0 Hz), 7.13 (1H, dd, J = 9.1, 2.6 Hz), 7.39 (1H, d, J = 2.6 Hz), 7.58 (1H, br s), 8.41 (1H, d, J = 9.1 Hz), 8.49 (1H, s).

The synthetic route of 1000574-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; AOKI, Kazumasa; MATSUI, Satoshi; YOSHIKAWA, Kenji; SHIMIZU,Hiroki; SASAKI, Junko; NAKAJIMA, Katsuyoshi; KANNO, Osamu; OIZUMI, Kiyoshi; EP2565185; (2013); 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. 202865-58-5, name is 1-Bromo-4,5-difluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., COA of Formula: C7H5BrF2O

To a flask containing 1-bromo-4,5-difluoro-2-methoxy-benzene (1.1 g, 4.93 mmol) and 1,4-dioxa-8-azaspiro[4.5]decane (0.78 g, 5.43 mmol) in 1,4-dioxane (10 mL) was added tBuONa (1.18 g, 12.33 mmol), Pd2(dba)3(92mg, 0.10 mmol) and Ru-Phos (92mg, 0.20 mmol)under N2. After being heated with stirring at 100 C overnight, the reaction mixture was cooled to rt, diluted with water (20 mL) and extracted with EA (30 mL) for three times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give 8- (4,5-difluoro-2-methoxy-phenyl)- 1 ,4-dioxa- 8-azaspiro [4.5] decane (1.31 g), which was used in the next step without further purification.

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
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Related Products of 2982-54-9,Some common heterocyclic compound, 2982-54-9, name is 2-(4-(Benzyloxy)phenyl)ethanamine hydrochloride, molecular formula is C15H18ClNO, 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 100 ml flask as added lH-pyrrolo[3,2-c]pyridine-2-carboxylic acid (100 mg and 0.617 mmol) 2-(4-(benzyloxy)phenyl)ethanamine HC1 (195 mg, 0.740 mmol) in DMF (10 ml) to give a light yellow suspension. HATU (352 mg, 0.925 mmol) and DIEA (319 mg, 2.467 mmol) were added. The mixture was stirred at RT for 16 hours. Added water and extracted with ethyl acetate (3 x 20 mL). The organic layers were combined and washed with water (3 x 20 mL). The organic was separated, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure The Biotage purification affordedl40 mg of the product (61%). ¾ NMR (DMSO-d6). delta 13.00 (s, 1H), 9.30 (s, 1H), 9.00 (m, 1H), 8.37 (d, H), 7.78 (d, 1H), 7.52(s, 1H), 7.30-7.47 (m, 5H), 7.18(d, 2H), 6.90(d, 2H), 5.02(s, 2H), 3.37(m, 2H0, 2.80(m, 2H). LC-MS: 472.25 (M+l)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-(Benzyloxy)phenyl)ethanamine hydrochloride, its application will become more common.

Reference:
Patent; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm; BUCKMELTER, Alexandre J.; CLODFELTER, Karl H.; HAN, Bingsong; KUNTZ, Judith D.; LIN, Jian; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; ZHENG, Xiaozhang; WO2012/154194; (2012); A1;,
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Synthetic Route of 151414-47-0,Some common heterocyclic compound, 151414-47-0, name is 2,6-Difluoro-4-methoxyaniline, molecular formula is C7H7F2NO, 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 mixture of 2,6-difluoro-4-methoxybenzenamine (0.98 g, 6.9 mmol) in toluene (20 mL) was added 6-chloro-3-pyridinecarboxaldehyde (1.0 g, 6.3 mmol). The reaction mixture was heated at reflux with the use of a Dean-Stark trap for azeotropic removal of water. After 16 h the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting material was dried in a vacuum oven at 55 C overnight to provide the title compound as a light brown solid (1.66 g).in NMR (CDCI3) delta 8.74 (s, 1H), 8.73 (d, J = 2.44 Hz, 1H), 8.32 (dd, J = 2.20 Hz, J= 8.29 Hz, 1H), 7.44 (d, J= 8.29 Hz, 1H), 6.59-6.52 (m, 2H), 3.82 (s, 3H)..9F NMR (CDCI3) delta -121.48 to -121.40 (m, 2F).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Difluoro-4-methoxyaniline, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; GREGORY, Vann; TAGGI, Andrew, Edmund; WO2011/56463; (2011); A2;,
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Synthetic Route of 50868-72-9, 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. 50868-72-9, name is 5-Methoxy-2-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: 3-Bromo-4-methylanisole To a suspension of 5-methoxy-2-methylanilme (5.00 g, 36.4 mmol) in water (144 mL) at 10 0C, was added cone H2SO4 (56 mL), while maintaining internal temperature below 25 0C. After 1 h at rt, the mixture was cooled to 3 0C and a solution of sodium nitrite (3.77 g, 54.7 mmol) in water (20 mL) was added dropwise over 30 mm, keeping the internal temperature below 5 0C After 1 h at 3 0C, the yellow heterogeneous mixture was poured into a 5 0C solution of CuBr (52.0 g, 364 mmol) in 48% aqueous HBr (260 mL). The dark mixture was heated at 60 0C for 2 h, allowed to cool to rt and extracted with Et2O (3x) (solid Na2S2O3 was added in the extraction process for partial decoloration). The combined organics were washed with 1 N NaOH (3x), 10% aq. Na2S2O3 and brine, dried (Na2SO4) and concentrated, affording the title compound as an orange liquid which was used without further purification in the next Step. 1H NMR (500 MHz, acetone-d6): delta 7.24 (d, IH), 7.14 (d, IH), 6.87 (dd, IH), 3.80 (s, 3H), 2.31 (s, 3H).

The synthetic route of 5-Methoxy-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2006/99735; (2006); 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. 10075-63-5, name is 1,5-Dimethoxynaphthalene, A new synthetic method of this compound is introduced below., Quality Control of 1,5-Dimethoxynaphthalene

General procedure: To a flask containing 1,3,5-trimethoxybenzene (1009.1 mg, 6 mmol) were added POCl3 (1011.9 mg, 6.6 mmol) and DMF (1754.1 mg, 24 mmol) at 0 C. After being stirred for 3 h at 40 C, DIH (2279.5 mg, 6 mmol) and aq ammonia (12 mL, 28-30%) were added to the reaction mixture. The obtained mixture was stirred for 3 h at rt. After the reaction, the mixture was poured into aq satd Na2SO3 solution and extracted with CHCl3 (3×20 mL). The organic layer was dried over Na2SO4, filtered, and evaporated to provide almost pure 2,4,6-trimethoxybenzonitrile (1156.1 mg) in 99% yield.

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; Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 68; 24; (2012); p. 4588 – 4595;,
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Electric Literature of 6850-60-8,Some common heterocyclic compound, 6850-60-8, name is (4-Ethoxyphenyl)methanamine, molecular formula is C9H13NO, 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: Synthesis of (2R, 3R, 4S, 5R)-2-(6-(benzylamino)-9H-purin-9-yl)-5-(hydroxymethyl) tetrahydrofuran-3,4-diol, 2. In a 7 mL MW vessel, 6-chloropurinoriboside 3 (20 mg, 0.07 mmol), benzylamine 4 (7.5 mg,0.07 mmol, 7.7 muL) and triethylamine (7.08 mg, 0.07 mmol, 9.8 muL)were mixed. The solid mixture was stirred in CEM Explorer. MWMethod: T = 210 C, Power: 300 W, Hold Time: 1 min, P = 250 PSI,Power Max activated. After cooling, the solvent was removed in vacuoand the crude was dissolved in methanol and then purified on PTLC(DCM/MeOH 9:1) to afford compound 2 as white solid (24 mg, 94%).C17H20N5O4: 358.1510; Found 358.1515. Rt: 8.92 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (4-Ethoxyphenyl)methanamine, its application will become more common.

Reference:
Article; Grimaldi, Manuela; Randino, Rosario; Ciaglia, Elena; Scrima, Mario; Buonocore, Michela; Stillitano, Ilaria; Abate, Mario; Covelli, Verdiana; Tosco, Alessandra; Gazzerro, Patrizia; Bifulco, Maurizio; Rodriquez, Manuela; D’Ursi, Anna Maria; Bioorganic Chemistry; vol. 98; (2020);,
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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 151414-47-0 as follows. Formula: C7H7F2NO

To a solution of 164 mg (0.372 mmol [calculation value with the purity defined as 100%]) of ethyl 5-(chioro- carbonyl)-6,6-dimethyl-3-[1 -(trimethylsilyl)cyclobutanecarboxamido]-5,6-dihydropyrrolo[3,4-c]pyrazole-2(4H)- carboxylate synthesized in the same way as in Reference Example 4 in 1.5 ml of 1,4-dioxane, 0.33 ml (1.9 mmol) of DIPEA and 516 mg (3.24 mmol) of 2,6-difluoro-4- methoxyaniline were added at room temperature in a nitrogen atmosphere and reacted at 1000 C. for 9.5 hours with stirring. Subsequently, the reaction solution was cooled to room temperature, and 0.20 ml (1.8 mmol) of N,N-dimethylethane- 1 ,2-diamine was added thereto at room temperature and then reacted at room temperature for 4 hours with stirring.10748] After completion of the reaction, ethyl acetate was added to the reaction solution, followed by washing with a 5% aqueous potassium bisulfate solution. Afier separation into an organic layer and an aqueous layer, the aqueous layer was subjected to extraction twice with ethyl acetate. The whole organic layer thus obtained was dried over anhydrous magnesium sulfate, then filtered, and concentrated under reduced pressure. The obtained concentration residue was subjected to preparative column chromatography (apparatus 1, DIOL silica gel, elution solvent: n-hexane:ethyl acetate=75:25-60:40-M5:55 (V/V)), and a fraction containing the compound of interest was concentrated under reduced pressure. The obtained concentration residue was subjected to preparative column chromatography (apparatus 1, silica gel, elution solvent: 1 ,2-dichloroethane:metha- nol=99:1-98:2-95:5 (V/V)), and a fraction containing the compound of interest was concentrated under reduced pressure. The obtained concentration residue was dissolved in ethyl acetate, then n-hexane was added thereto, and the deposited solid was collected by filtration, washed with n-hexane, and then dried under reduced pressure to obtain 105 mg of the title compound (yield: 57% [calculation value with the purity of the starting material defined as 100%]) as a white solid.10749] Mass spectrum (CI, mlz): 492 [M+1].10750] ?H-NMR spectrum (400 MHz, DMSO-d5) oe: 12.26 & 11.72 (br s, total 1H), 9.59 (s, 1H), 7.80-7.59 (m, 1H), 6.79-6.69 (m, 2H), 4.64-4.47 (m, 2H), 3.77 (s, 3H), 2.56-2.40 (m, 2H), 2.28-2.11 (m, 2H), 1.92-1.71 (m, 2H), 1.69-1.53 (m, 6H), 0.13-0.05 (m, 9H).

According to the analysis of related databases, 151414-47-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UBE INDUSTRIES, LTD.; IWASE, Noriaki; AGA, Yasuhiro; USHIYAMA, Shigeru; KONO, Shigeyuki; SUNAMOTO, Hidetoshi; MATSUSHITA, Takashi; OGI, Sayaka; UMEZAKI, Satoshi; KOJIMA, Masahiro; ONUMA, Kazuhiro; SHIRAISHI, Yusuke; OKUDO, Makoto; KIMURA, Tomio; (165 pag.)US2018/186818; (2018); A1;,
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