Author: tianli

These common heterocyclic compound, 863127-76-8, name is (E)-N-(2-Chloro-6-methylphenyl)-3-ethoxyacrylamide, 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. 863127-76-8

Example 2[0157] To a mixture of compound 1 (5.30 g, 22.11 mmol) in 1,4-dioxane (100 mL) and water (70 mL) was added NBS (4.40 g, 24.72 mmol) at -10 to 0 C. The slurry was warmed and stirred at 20-22 C for 3 h. Thiourea (1.85 g, 26.16 mmol) was added and the mixture heated to 100 C. After 2 h, the resulting solution was cooled to 20-22 C and cone, ammonium hydroxide (6 mL) was added drop wise. The resulting slurry was concentrated under vacuum to about half volume and cooled to 0-5 C. The solid was collected by vacuum filtration, washed with cold water, and dried to give 5.4 g (90% yield) of compound 2 as deep-yellow solids. 1H NMR (500 MHz, DMSO-d6) delta 2.19 (s, 3H), 7.09-7.29 (m, 2H, J=7.5), 7.29-7.43 (d, IH, J=7.5), 7.61 (s, 2H), 7.85 (s, IH), 9.63 (s, IH); ESI-MS: calcd for (C?HioClN3OS) 267, found 268 MH+).

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 863127-76-8.

Reference:
Patent; ABRAXIS BIOSCIENCE, LLC; TAO, Chunlin; WANG, Qinwei; NALLAN, Laxman; POLAT, Tulay; KORONIAK, Lukasz; DESAI, Neil; WO2010/144338; (2010); A1;,
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19982-07-1, Adding some certain compound to certain chemical reactions, such as: 19982-07-1, name is N-(3,5-Dimethyladamantan-1-yl)acetamide, 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 19982-07-1.

l-Acetamido-3,5-dimethyl adamantane (40.0 g) was added to reaction vessel followed by addition of sodium hydroxide (57.80 g) and DEG (200 mL) at 25-300C. The reaction mixture was stirred and then heated at 155-1700C and heating was maintained for 10 Hrs. The reaction mixture was cooled to 80-850C and water (1600 mL) was added within 1 Hr. Reaction mixture was stirred for 30 minutes and toluene (500 mL) was added to the reaction mixture and further stirred for 1 Hr. After stirring the layers were settled for 30 minutes and then separated out. The organic (Toluene) layer was kept and to the aqueous layer, toluene (300 mL) was added and stirred for 1 Hr and after stirring layers were settled and separated out. Total toluene layers were collected and water (500 mL) was added to it and stirred for 1 Hr at 25-300C. After stirring the layers were settled for 30 minutes and then separated out. Organic (toluene) layer was dried over anhydrous sodium sulfate and wash the bed with toluene (50 mL)and then toluene was distilled under reduced pressure below 600C to afford the title compound Memantine Base.; Example 3 (b): Preparation of Memantine Base (One pot synthesis) l~Bromo-3,5-dimethyl adamantane (60.0 g) was added to reaction vessel followed addition of acetamide (87.42 g) the reaction mixture was stirred and heated at 130-1400C for 3 to 5 Hrs. The reaction mixture was cooled up to 80- 850C and then toluene (300 mL) was added to reaction mixture and stirred for 1 Hr. The reaction mixture was treated with water (600 mL) and stirred for lhr. The reaction mixture was filtered and washed with toluene. The organic layer was separated and toluene was distilled out at temperature range 105-130C.Cool to 105-1150C and the reaction mass was again treated with DEG(270 mL) at 105-1150C maintaing 105-1150C for 2 hrs. Again distill out toluene at 130-140C.Cool at 105-1150C and add sodium hydroxide (78 g) was added at 105-1150C. The reaction mixture was stirred and then heated at 155-1700C and heating was maintained for 10 Hrs. The reaction mixture was cooled to 80-850C and water (200 mL) was added within 1 Hr. Reaction mixture was stirred for 30 minutes and toluene (400 mL) was added to the reaction mixture and further stirred for 1 Hr. After stirring the layers were settled for 30 minutes and then separated out. The organic (Toluene) layer was kept and to the aqueous layer, toluene (50 mL) was added and stirred for 1 Hr and after stirring layers were settled and separated out. Total toluene layers were collected and water (500 ml) was added to it and stirred for 1 Hr at 25-300C. After stirring the layers were settled for 30 minutes and then separated out to afford the title compound Memantine Base.

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 19982-07-1.

Reference:
Patent; CADILA HEALTHCARE LIMITED; WO2008/62472; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, I believe this compound will play a more active role in future production and life. 112101-81-2

10 g of (-)- (R)-5- (2- (2- (2-ethoxyphenoxy) ethylamino)-1-propyl)-2-methoxybenzene sulphonamide hydrochloride (TH) from Example 2 is recrystallised from mixtures of methanol and ethanol. Analysis : Methanol HPLC-composition Quantity of Yield HPLC-composition to ethanol of the starting raw solvent of the product* ratio material* used 100 : 0 TH 86. 1 % 120 mi 7. 77 g TH 95. 84 % impurity (2) 1. 53 % (77. 7 %) impurity (2) 0. 09 % impurity (3) 2. 84 % impurity (3) 0. 0 % impurity (4) 1. 79 % impurity (4) 0. 24 % impurity (5) 0. 98 % impurity (5) 0. 05 % impurity (6) 6. 17 % impurity (6) 3. 73 % 90 : 10 TH 86. 1 % 75 g TH 95. 5% impurity (2) 1. 53 % (77, 5%) impurity (2) 0. 12 % impurity (3) 2. 84 % impurity (3) 0. 0 % impurity (4) 1. 79 % impurity (4) 0. 31 % impurity (5) 0. 98 % impurity (5) 0. 08 % impurity (6) 6. 17 % impurity (6) 3. 94 % 70 : 30 TH 86. 1 % 210 ml 7, 78g TH 95. 9 % impurity (2) 1. 53 % (77. 8 %) impurity (2) 0. 12 % impurity (3) 2. 84 % impurity (3) 0. 0 % impurity (4) 0. impurity 0. 31 % impurity (5) 1. 79 % impurity (5) 0. 08 % impurity (6) 6. 17 % impurity (6) 3. 49 % 50 : 50 TH 86. 1 % 340 ml 7. 41 g TH 99. 27% impurity (2) 1. 53 % (74. 1 %) impurity (2) 0. 15 % impurity (3) 2. 84 % impurity (3) 0. 0 % impurity (4) 0. 98 % impurity (4) 0. 32 % impurity 1. 79 % impurity (5) 0. 08 % impurity (6) 6. 17 % impurity (6) 0. 0 % 30 : 70 TH 86. 1 % 500 ml 7. 55 g TH 99. 28 % impurity (2) 1. 53 % (75. 5 %) impurity (2) 0. 17 % impurity (3) 1. 79 % impurity (3) 0. 0 % impurity (4) 0. 98 % impurity (4) 0. 32 % impurity (5) 1. 79 % impurity (5) 0. 10 % impurity (6) 6. 17 % impurity (6) 0. 0 % * impurity (2) = 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide impurity (3) = 2-(2-ethoxyphenoxy) ethylbromide impurity (4) = N-(2-(2-ethoxyphenoxy) ethyl)-5-(2-(2-(2-ethoxyphenoxy) ethyl) amino)-1-propyl)-2-methoxybenzenesulphonamide impurity (5) = 5-(2-(bis-(2-(2-ethoxyphenoxy) ethyl) amino)-1-propyl)-2-methoxybenzenesulphonamide impurity (6) = 1,2-bis (2-ethoxyphenoxy) ethane (6)

The chemical industry reduces the impact on the environment during synthesis 112101-81-2. I believe this compound will play a more active role in future production and life.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; WO2005/63702; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

45267-19-4, 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. 45267-19-4, name is N-(3-(Dimethylamino)propyl)tetradecanamide, A new synthetic method of this compound is introduced below.

EXAMPLE 1 Preparation of a UV-Light-Absorbing Quaternary Polysiloxane According to the Invention and of the General Formula 5.5 g (0.0176 mol) of a tertiary amine of the general formula: are initially introduced together with 1.9 g (0.032 mol) of acetic acid and 16.5 g of cinnamic acid (0.111 mmol) and 30 ml of isopropanol into a 250 ml four-necked flask fitted with stirrer, dropping funnel, thermometer and reflux condenser. After 5 minutes, 42 g (0.14 mol of epoxy) of an epoxysiloxane of the general formula: are added dropwise, heated to reflux temperature and stirred for 6 hours. The mixture is then distilled at 100 C. under reduced pressure. A high-viscosity, yellow-brown product is obtained.

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; Ferenz, Michael; Gruening, Burghard; Leidreiter, Holger; Messinger, Erika; Pascaly, Matthias; Zuendorff, Astrid; US2006/188456; (2006); A1;,
Amide – Wikipedia,
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The chemical industry reduces the impact on the environment during synthesis 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, I believe this compound will play a more active role in future production and life. 107017-73-2

To a solution of tert-butyl (l-(hydroxymethyl)cyclopropyl)carbamate (commercial, 15 g; 80.3 mmol) in DCM (235 mL), cooled to -20C, was slowly added DIPEA (45 mL; 263 mmol) over 15min. A solution of Pyr.S03 (38.75 g; 110 mmol ) in DMSO (108 mL; 1.52 mol) was added dropwise over 45min. The reaction mixture was stirred at 0C for 2h45. The reaction mixture was partitioned between water (1 L) and DCM (200 mL). The two layers were separated and the aq. layer was extracted once more with DCM (300 mL). The evaporation residue was purified by CC (Hept-EA) to afford the title compound (13.18 g; 89% yield) as a white solid. 1H NMR (d6-DMSO) delta: 8.99 (s, 1H); 7.55 (s, 1H); 1.44-1.31 (overlapped m, 2H); 1.39 (s, 9H); 1.19-1.10 (m, 2H). MS (ESI, m/z): 186.2 [M+H+] for C9H15N03; tR = 0.62 min

The chemical industry reduces the impact on the environment during synthesis 107017-73-2. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CHAPOUX, Gaelle; DIETHELM, Stefan; GAUVIN, Jean-Christophe; PANCHAUD, Philippe; SURIVET, Jean-Philippe; (90 pag.)WO2017/37039; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone, A new synthetic method of this compound is introduced below., 61903-11-5

A solution of N-(4-(5-(difluoromethyl)- 1,3 ,4-oxadiazol-2-yl)benzyl)-N-phenylethenesulfonamide (0.100 g, 0.255 mmol), N-acetylhomopiperazine (0.073 g, 0.511 mmol) and N,N-diisopropylethylamine (0.176 mL, 1.022 mmol) in dichioromethane (5 mL) was stilTed at the room temperature for 18 hr. Then, water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 12 g cartridge; methanol / dichloromethane = 3 % to 5 %) to give2-(4-acetyl- 1 ,4-diazepan- 1 -yl)-N-(4-(5-(difluoromethyl)- 1,3 ,4-oxadiazol-2-yl)benzyl)- N-phenylethane-1-sulfonamide as white solid (0.032 g, 23.5 %).?H NMR (700 MHz, CDC13) oe 8.04 – 8.00 (m, 2 H), 7.45 (d, 2 H, J = 8.3 Hz), 7.36 -7.27 (m, 5 H), 6.91 (t, 1 H, J= 51.7 Hz), 4.96 (s, 2 H), 3.68 – 3.66 (m, 1 H), 3.64- 3.59(m, 1 H), 3.56 – 3.51 (m, 2 H), 3.36 – 3.33 (m, 1 H), 3.32 – 3.27 (m, 1 H), 3.13 – 3.07(m, 2 H), 2.79-2.66 (m, 4 H), 2.11 -2.09 (m, 3 H), 1.97 (m, 1 H), 1.88 – 1.87 (m, 1H);LRMS (ES) mlz 534.3 (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; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

625-51-4, A common compound: 625-51-4, name is N-(Hydroxymethyl)acetamide, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

EXAMPLE 5 40.8 g (0.4 mol) of acetic anhydride were cooled to 10 C. After this, 16.4 g (0.2 mol) of phosphorous acid were introduced in the course of 5 minutes, with stirring and cooling. 17.8 g (0.2 mol) of N-hydroxymethylacetamide were subsequently added dropwise at 10 C. in the course of 10 minutes. After this, the mixture was first allowed to come to room temperature and then refluxed for 2.5 hours. The mixture was subsequently cooled. 10 ml of water were then added in portions. After this, the mixture was kept under reflux for 1 hour. After this, a mixture of 10 ml of acetic acid and 1.5 ml of water was added, and stirring was continued. After crystallisation and filtration with suction, 16.3 g (53% of theory) of acetylaminomethanephosphonic acid of a melting point of 188-194 C. were obtained.

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, N-(Hydroxymethyl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoechst Aktiengesellschaft; US5432291; (1995); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

127828-22-2, Name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, 127828-22-2, belongs to amides-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.

To a solution of mono-Boc protected diamine linker (0.1 mmol, 1 eq) and Imatinib- COOH (54 mg, 0.1 mmol, 1 eq) in DMF (1 mL), COMU (43 mg, 1 mmol, 1 eq) and DIPEA (48 m L ) were added. The reaction mixture was stirred at room temperature for 1 hour, then quenched with ice cold water. Volatiles were removed in vacuum and the crude mixture was purified by preparative HPLC (METHOD 2). Fractions containing the desired product were evaporated under reduced pressure and the residue was dissolved in DCM (1 mL) and treated with a solution of anhydrous HCl in dioxane (4M, 1 mL). After 1 hour, volatiles were removed under reduced pressure and the residue was freeze dried in order to remove any excess of acid. Analytical data (HRMS) are provided in table V shown below.

Statistics shows that tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate is playing an increasingly important role. we look forward to future research findings about 127828-22-2.

Reference:
Patent; UNIVERSITY OF DUNDEE; CIULLI, Alessio; TESTA, Andrea; HUGHES, Scott; BUTCHER, Steven Peter; (337 pag.)WO2019/238817; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

402-46-0, 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. 402-46-0, name is 4-Fluorobenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

INTERMEDIATE 12; This shows the preparation of 4-(4-chlorophenoxy)benzenesulfonamide.To a solution of 4-chlorophenol (128 mg) and 4-fluorobenzenesulfonamide (175 mg) in NMP (1 mL) was added caesium carbonate (326 mg) and the mixture was heated in a CEM Discover microwave at 130 C for 10 minutes. The reaction mixture was allowed to cool , and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over sodium sulfate. The filtrate was concentrated in vacuo, and the resulting brown oil was dissolved in diethyl ether and flashed through a short plug of silica. Concentration in vacuo gave an oil that was subjected to column chromatography, eluting with 30% ethyl acetate in iso-hexane to give the title compound 4-(4- chlorophenoxy)benzenesulfonamide (100 mg) as a waxy solid.1H NMR (300 MHz, DMSO) delta 7.92 – 7.82 (m, 4H), 7.52 (dd, 2H), 7.47 – 7.40 (m, 2H), 7.34 (br s, 2H).

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

Reference:
Patent; ASTRAZENECA AB; WO2006/75955; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 121492-06-6 as follows. 121492-06-6

DMF (20 ml), QHL 014 (4.42 g, 9.2 mmol), N-BOC-N-methyl ethylenediamine (2.00 g, 12.5 mmol), HATU (4.20 g, 11 mmol) was added in a 50 ml single-necked flask. After stirring for 5 minutes, DIPEA (5 ml, 27.6 mmol) was added dropwise. Stir at room temperature until QHL014 is completely reacted. DMF was evaporated under reduced pressure, and the crude product was dissolved in ethyl acetate and washed with water. The organic phase was dried and purified by silica gel column chromatography (dichloromethane: methanol = 50:1 to 20:1) to obtain light yellow solid QHL 015 (4.81 g, yield 80%).

According to the analysis of related databases, 121492-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yafei Shanghai Biolog Medicine Science & Technology Co., Ltd.; LIU, Yuan; LIU, Cheng; WANG, Haiyang; (43 pag.)EP3572420; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics