Tag: M.W=100-200

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. 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 7252-83-7

To an ice cooled solution of sodium ethoxide (3.26 g, 48.0 mmol) in ethanol (25.0 mL) was slowly added 4-methoxybenzenethiol (6.73 g, 48.0 mmol). The reaction mixture was stirred for 15 min. 2-Bromo-l,l-dimethoxyethane (5.64 mL, 48.0 mmol) was added, and the reaction mixture was refluxed for 2 h. After the precipitate was isolated by filtration, the mother liquor was evaporated under reduced pressure. The resultant residue was diluted with diethyl ether (100 mL) and washed with water and brine, dried over sodium sulfate, filtered, and concentrated to give the desired crude product (11.0 g) which was directly used in next step reaction without further purification. 1H-NMR (400 MHz, CDCl3): 7.40 (m, 2H), 6.85 (m, 2H), 4.47 (t, J = 5.6 Hz, IH), 3.80 (s, 3H), 3.34 (s, 6H), 3.01 (d, J = 5.6 Hz, 2H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 7252-83-7.

Reference:
Patent; INCYTE CORPORATION; ZHUO, Jincong; METCALF, Brian; WO2008/64157; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 2393-23-9, 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. 2393-23-9, name is 4-Methoxybenzylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of p-anisaldehyde (146 mmol) in ethanol (500 mL) was added 4- methoxybenzylamine (146 mmol). The mixture was then cooled in an ice water bath. NaBH4 (294 mmol) was added in portions and the reaction mixture was allowed to warm to rt, gradually. Ice water slush (100 mL) was added and the mixture was concentrated to half its original volume. The mixture was then extracted with ether and the organics were combined, washed with brine, dried, and concentrated. Hexane (~50 mL) was added and the precipitate was filtered to give 35 g of bis-(4-methoxy-benzyl)-amine, 19, as white solid.

The synthetic route of 4-Methoxybenzylamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2006/81554; (2006); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 1116-77-4, These common heterocyclic compound, 1116-77-4, name is 4,4-Diethoxy-N,N-dimethyl-1-butanamine, 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.

(ii) Preparation of crude rizatriptan benzoate; Into a clean IOOL glass reactor were charged water (20L) cone. HCl (8.5L), and l-(4- aminophenylmethyl)-l,2,4-triazole (5.0Kg). The reaction mass was stirred for 20-30min at 25-30 C and cooled to 0-5 C. Aqueous sodium nitrite (2.1Kg in 3.0Lof water) was added to the reaction mass below 5C over a period of 2hr. The reaction mass was maintained below 50C for lhr.Into a clean, 200L glass reactor were charged water (30 L) and sodium sulfite (9.0 Kg) under nitrogen atmosphere at 25-30 C. The resulting solution was cooled to below 10 C. Above diazonium salt solution was added to the reaction mass in 20-30 min period keeping the temperature below 10 C. The reaction mass was slowly heated to 65-7O0C over a period of 2.5-3. Ohr. After maintaining at this temperature for 2hr sulfuric acid EPO (7.2L) was added to the reaction mixture and continued the maintenance at same temperature for 2.0-2.5 hr. The reaction mass was cooled to reach 20-25 0C.4-Dimethylaminobutyraldehyde diethyl acetal (7.8 kg) was added to the reaction mass in 30-45min keeping the temperature at 25-30 C. The reaction mass was maintained at this temperature for 4-5hr. TLC of the reaction mass indicated the absence of starting material. The reaction mass was heated to 35-400C and maintained for lhr. Temperature of the reaction mass was further raised to 60-65C and maintained for 3.5hr. The reaction mass was cooled to 20-30C and adjusted the pH of reaction mass to 6.5-7.0 with ammonia solution. Ethyl acetate (15L) was added to the reaction mass and stirred for 15- 20min and separated the organic layer. Aqueous layer pH was adjusted to 8.5-9.0 with ammonia solution. Aqueous layer was extracted with ethyl acetate (3 x 35L). Combined ethyl acetate layer was treated with activated carbon (lkg) and distilled of solvent under reduced pressure to get 4.7kg crude rizatriptan base as oil.The above crude rizatriptan base was dissolved in 18L of acetone at 25-30 0C. Benzoic acid (2.1kg) was added to the reaction mass at 25-30 C. After stirring for 45-60min at 25-30 C the reaction mixture was cooled to below 0 C and maintained for 10-12hr. The reaction mass was allowed to reach 20-25 0C and maintained for 2.5hr- before filtration. The wet cake was washed with 3.5L of acetone. Drying at 50-60 C gave 3kg of rizatriptan benzoate.; Example 4; Preparation of rizatriptan benzoate; (i) Preparation of crude rizatriptan benzoate:; Into a clean IOOL glass reactor were charged water (30L)5 cone. HCl (15kg), and l-(4- aminophenylmethyl)-l,2,4-triazole (7.5Kg). The reaction mass was stirred for 20-30min at 25-30 0C and cooled to below 0 C. Aqueous sodium nitrite (3.2Kg in 5Lof water) was added to the reaction mass below 5C over a period of 2hr. The reaction mass was maintained below 5C for lhr.Into a clean, 200L glass reactor were charged water (45 L) and sodium sulfite (13.5 Kg) under nitrogen atmosphere at 25-30 C. The resulting solution was cooled to below 10 0C. The above prepared diazonium salt solution was added to the reaction mass in 20-30 min period keeping the temperature below 10 C. The reaction mass was slowly heated to 65-70C over a period of 2.5-3.Ohr. After maintaining at this temperature for 2hr sulfuric acid (19.8kg) was added to the reaction mixture and continued the maintenance at same temperature for 2.0-2.5 hr. The reaction mass was cooled to reach 20-25 0C.4-Dimethylaminobutyraldehyde diethyl acetal (11.7 kg) was added to the reaction mass in 30-45min keeping the temperature at 25-30 0C. The reaction mass was maintained at this temperature for 4-5hr. TLC of the reaction mass indicated the absence of starting material. The reaction mass was heated to 35-40C and maintained for lhr. Temperature of the reaction mass was further raised to 60-65C and maintained for 3.5hr. The reaction mass was cooled to 20-30C and adjusted the pH of reaction mass to 6.5-7.0 with ammonia solution. Ethyl acetate (15L) was added to the reaction mass and stirred for 15-20min and separated the organic layer. Aqueous layer pH was adjusted to 8.8-9.2 with ammonia solution. Aqueous layer was extracted with ethyl acetate (3 x 45L). Combined ethyl acetate layer was treated with activated carbon (1.5kg) and distilled of solvent under reduced pressure to get 7.5kg of crude rizatriptan base as oil. EPO The above crude rizatriptan base was dissolved in 3OL of acetone at 25-30 0C. Benzoic acid (3.5kg) was added to the reaction mass at 25-30 C. After stirring for 45-60min at 25-30 C the reaction mixture was cooled to below 0 C and maintained for 10-12hr. The reaction mass was allowed to reach 20-25 C and maintained for 2.5hr before filtration. The wet cake was washed with 5L of acetone. Drying at 50-60 0C gave 4.5kg of rizatriptan benzoate.

Statistics shows that 4,4-Diethoxy-N,N-dimethyl-1-butanamine is playing an increasingly important role. we look forward to future research findings about 1116-77-4.

Reference:
Patent; NATCO PHARMA LIMITED; PULLA REDDY, Muddasani; SATYASRINIVAS, Hanumara; RADHARANI, Kagitha; VENKAIAH CHOWDARY, Nannapaneni; WO2006/137083; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, 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 1836-62-0, Recommanded Product: 1836-62-0

2- (2-methoxyphenoxy) ethanamine (851 mg, 5.1 mmol),Benzaldehyde (540 mg, 5.1 mmol),Para-Toluenesulfonic acid (PTSA, 105 mg, 0.55 mmol) was dissolved in 5 mL of toluene.The mixed solution was refluxed, maintained and stirred.TLC (Thin Layer Chromatography) was used to confirm the completion of the reaction, and then the temperature was lowered to room temperature.The mixture was separated using water and ethyl acetate, and washed with a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulphate and concentrated in vacuo to give crude product.The crude product prepared from the above was dissolved again in methanol (10 ml) at 0 C. Sodium borohydride (250 mg, 6.6 mmol) was slowly added dropwise and the temperature was raised to room temperature. After 24 hours of reaction, the mixture was diluted with dichloromethane and water. The diluted solution was extracted, separated and washed with a saturated aqueous sodium chloride solution three times. It was then dried over magnesium sulfate, concentrated in vacuo, and purified by flash column chromatography on silica gel, 10-50% ethyl acetate / hexane to finally yield the desired compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-Methoxyphenoxy)ethylamine, and friends who are interested can also refer to it.

Reference:
Patent; Gachon University Industry Academy Cooperation Foundation; Kim Mi-hyeon; Kim Seon-yeo; Jang Cheong-yun; (29 pag.)KR2018/125090; (2018); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 5961-59-1, name is 4-Methoxy-N-methylaniline, molecular formula is C8H11NO, 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. Recommanded Product: 4-Methoxy-N-methylaniline

HATU (1.5 g, 4.0 mmol) was added to a stirred solution of 4-methoxy-N-methylaniline mg, 3.64 mmol) and (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (1.06 g, 4.0 mmol) in DMF (20 mL) and DIPEA (1.3 mL, 7.3 mmol) and the reaction mixture was stirred at rt for 4h. The reaction was concentrated and the residual crude oil was partitioned between EtOAc (-60 mL) and 1/2 sat. NaHCC (aq) (-60 mL). The organic component was washed with brine (-40 mL), dried (MgS04), filtered, concentrated and purified using a Biotage Horizon (80 g SiC , 10-40% EtOAc/hexanes) to yield Intermediate JB-1 (1.34 g) as a clear amber viscous oil. LC-MS retention time = 3.17 min; m/z = 385.3 [M+H]+. (Column: Phenonenex-Luna C18 2.0 x 50mm 3 muiotaeta. Solvent A = 95% Water:5% Acetonitrile: 10 mM NH4OAc. Solvent B = 5% Water:95% Acetonitrile: 10 mM NH4OAc. Flow Rate = 0.8 mL/min. Start % B = 0. Final % B = 100. Gradient Time = 4 min. Wavelength = 220). NMR (400 MHz, CDCh) delta 7.25 – 7.20 (m, 3H), 7.03 – 6.64 (m, 6H), 5.20 (d, J=8.8 Hz, 1H), 4.53 (app q, J=7.4 Hz, 1H), 3.83 (s, 3H), 3.18 (s, 3H), 2.89 (dd, J=13.1, 7.5 Hz, 1H), 2.71 (dd, J=13.1, 6.5 Hz, 1H), 1.39 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5961-59-1, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 41864-45-3, name is 4,5-Dimethoxy-2-methylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 41864-45-3

EXAMPLE 157 4-(4,5-Dimethoxy-2-methylanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine The title compound was prepared from a mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 4,5-dimethoxy-2-methylaniline (48 mg, 0.290 mmol) similar to Example 117 and isolated as a red solid (8 mg, 11%). 1H NMR (CDCl3): 9.69 (s, 1H), 8.74-8.68 (m, 2H), 7.56 (s, 1H), 7.43-7.39 (m, 1H), 6.84 (s, 1H), 6.83 (s, 1H), 6.46 (s, 1H), 3.94 (s, 3H), 3.86 (s, 3H), 2.23 (s, 3H).

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; Cytovia, Inc.; US2003/69239; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 393-15-7, name is 4-Methoxy-3-(trifluoromethyl)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 393-15-7, category: ethers-buliding-blocks

4-Methoxy-3-trifluoromethyl-phenylamine (5 g, 26 mmol) in 12 mL water was cooled to -5 degrees C (Ice/Methanol bath). Conc. HCl was added dropwise (7 ml), and the reaction mixture was stirred for five minutes. A solution of NaNO2 (2.0 g, 29 mmol) dissolved in 3 ml water was added dropwise over 10 minutes, and the reaction mixture was tirred for 30 min. Sodium acetate (1.8 g, 22 mmol) was then added, and stirring was continued at -5 degrees C. In a separate flask, ethyl alpha-acetoacetate (4.55 g, 29 mmol) in 20 ml absolute ethanol was stirred, and KOH (1.6 g, 29 mmol) dissolved in 3 ml water was added, followed by ice (30 g). The resulting diazonium salt was added quickly to the reaction mixture, rinsing in with 5 ml EtOH, and the reaction mixture was stirred at zero degrees C for 3.5 hours, then stored at -10 C) for 16 hours. The reaction mixture was warmed to room temperature and extracted with ethyl acetate, washed with brine, and dried over magnesium sulfate. Solvent was removed under reduced pressure to leave a liquid residue. In a separate flask 100 ml EtOH and 21 ml acetyl chloride were mixed, with cooling in an ice bath, then heated to 70 degrees C. The liquid residue was added via pipette over 15 minutes to the acetyl chloride solution. This reaction mixture was heated to reflux for 2.5 hours, cooled, evaporated under reduced pressure. The residue was purified by colunm chromatography (10% ethyl acetate/hexane) to give 3.0 g 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester, 38% as a white solid. and triturated with diethyl ether to give 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (1.0 g) as a white solid, and 5-Methoxy-3-methyl-4-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (14% ) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methoxy-3-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Roche Palo Alto LLC; US2005/209260; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 6443-69-2,Some common heterocyclic compound, 6443-69-2, name is 1,2,3-Trimethoxy-5-methylbenzene, molecular formula is C10H14O3, 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: BF3¡¤Et2O was slowly added dropwise, to a stirred solution of polyhydroxy or polymethoxy phenols and alkyl alchol in dioxane at 0C. After the addition was completed, the stirring was continued for 3h at room temperature. The mixture was poured water and extracted with EtOAc. The organic layer was dried over Na2SO4 and filtered. The solvent was evaporated under reduced pressure. The crude was chromatographed on silica gel.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2,3-Trimethoxy-5-methylbenzene, its application will become more common.

Reference:
Article; Kamauchi, Hitoshi; Oda, Takumi; Horiuchi, Kanayo; Takao, Koichi; Sugita, Yoshiaki; Bioorganic and Medicinal Chemistry; vol. 28; 1; (2020);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

171290-52-1, name is 3,5-Dimethoxyphenylacetylene, 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. name: 3,5-Dimethoxyphenylacetylene

A mixture of (S)-3-(5-amino-3-bromo-4-cyano-1H-pyrazol-1-yl)pyrrolidine-1-carboxylic acid tert-butyl ester 7c (5 g, 14.1 mmol), cuprous iodide (0.6 g, 2.8 mmol), triethylamine (9 mL), [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride (2 g, 2.8 mmol) and N,N-dimethylformamide (150 mL) was heated to 80 C. under argon, and then 1-ethynyl-3,5-dimethoxybenzene (14 g, 84.5 mmol) was added in portions, next stirred for 2 hours, and then cooled to room temperature, poured the reaction solution into water, extracted with ethyl acetate (200 mL*3); next the organic phases were combined and dried over anhydrous sodium sulfate, the desiccant was removed by filtering, and the reaction system was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=5/1), so as to obtain the title product (S)-3-(5-amino-4-cyano-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazol-1-yl)pyrrolidine-1-carboxylic acid tert-butyl ester 7d (5 g, brown oil), and the yield was 81%. MS m/z (ESI): 382[M+1-56]

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEIJING INNOCARE PHARMA TECH CO., LTD.; Chen, Xiangyang; Gao, Yingxiang; Kong, Norman Xianglong; (59 pag.)US2019/210997; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 3616-56-6, 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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis Example B17Synthesis of 8-bromo-12H-benzofuranyl[2,3-a]carbazole (compound 17)Under nitrogen, compound 16 (4.6 g, 1 eq) is initially charged and dissolved with acetic acid (185 ml) while heating to reflux.Then (dimethylamino)acetaldehyde diethyl acetal (95percent; 25 g, 10 eq.) is added dropwise to the reaction within 1 h and the mixture is stirred at reflux for 7 h.The mixture is cooled to room temperature and diluted with methylene chloride.In a separating funnel, the organic phase is washed with distilled water and then with saturated NaCl solution.The organic phase is dried with sodium sulfate and concentrated. LC (reverse phase, acetonitrile) gives 1.35 g of product (27.3percent yield).1H NMR (CD2Cl2; 400 MHz): delta=8.73 (s, 1H), 8.17 (s, 1H), 8.16 (d, 1H), 8.08 (d, 1H), 7.78 (d, 1H), 7.60 (d, 1H), 7.56 (m, 2H), 7.49 (dd, 1H), 7.31 (dd, 1H).

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

Reference:
Patent; BASF SE; OSRAM OPTO SEMICONDUCTORS GMBH; KONINKLIJKE PHILIPS ELECTRONICS N.V.; US2011/266528; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem