Tag: M.W=100-200

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;,
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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. 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;,
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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;,
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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 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;,
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915087-25-1, The chemical industry reduces the impact on the environment during synthesis 915087-25-1, name is 4-Amino-2-fluoro-N-methylbenzamide, I believe this compound will play a more active role in future production and life.

Compound I (100 g, 0.594 mol) is suspended in 300 mL of dioxane. TEA (250 mL, 3.59 mol) is added by pouring in a thin stream. The system is placed under nitrogen, and heated to 60C. A solution of intermediate II (160 g, 0.90 mol) in 150 mL of dioxane is prepared separately. The solution of compound II is added to the suspension in the reactor and left to react for about 20 hours. The mixture is cooled to l5C and filtered through a Biichner funnel, washing the cake twice with 100 mL of dioxane each time. The resulting product is suspended in 1200 mL of water, 1M HC1 is added until a pH < 3 is reached, and the resulting suspension is then filtered through a Buchner funnel, washing the cake twice with 200 mL of water each time. The crystal thus isolated is dried under vacuum at the temperature of 60C, providing intermediate III in a 76% yield (120 g, 45.1 mmol) and 99.6% HPLC purity. NMR (300MHz, CDCh) d 15.3 (m, 4H), 2.58 (t, br, 2H), 2.73 (s, 3H), 6.00 (m, 1 H), 6.22 (s, 1 H), 7.17 (s, 1H), 7.46 (s, 1H), 7.65 (d, 1H), 12.63 (m, 1H). The chemical industry reduces the impact on the environment during synthesis 4-Amino-2-fluoro-N-methylbenzamide. I believe this compound will play a more active role in future production and life. Reference:
Patent; OLON S.P.A.; GRANDE, Valentina; FERRETTI, Gabriele; NOVO, Barbara; (0 pag.)WO2019/229625; (2019); A1;,
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2675-89-0, Name is 2-Chloro-N,N-dimethylacetamide, 2675-89-0, 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.

Preparation 2: (2184) To a solution of (2185) 6-(3-isopropyl-5-(piperidin-4-yl)-lH-indol-2-yl)-8-methoxy-[l,2,4]triazolo[l,5-a]pyridin e, HC1 (30.6 g, 71.8 mmol) in a DMF (700 mL) solvent mixture were added (2186) 2-chloro-N,N-dimethylacetamide (9.62 mL, 93 mmol) and TEA (50.1 mL, 359 mmol) at room temperature. The reaction mixture was stirred at room temperature for 12 h. The starting material was converted to product. Next, water (2 L) was added to the above solution, the upper layer and the lower layer were extracted with ethyl acetate. The combination of the organic layers was washed with brine, dried and concentrated to give a solid, which was purified by recrystallization from ethanol to afford (2187) 2-(4-(3-isopropyl-2-(8-methoxy-[l,2,4]triazolo[l,5-a]pyridin-6-yl)-lH-indol-5-yl)piperid in-l-yl)-N,N-dimethylacetamide (28.3 g, 59.3 mmol, 83 % yield). LCMS MH+: 475.2. HPLC Ret. Time 0.66 min. Method G. C: 68.28%, H: 7.19%, N: 17.63%.

Statistics shows that 2-Chloro-N,N-dimethylacetamide is playing an increasingly important role. we look forward to future research findings about 2675-89-0.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; HAQUE, Tasir Shamsul; LOMBARDO, Louis J.; MACOR, John E.; MUSSARI, Christopher P.; PASUNOORI, Laxman; RATNA KUMAR, Sreekantha; SHERWOOD, Trevor C.; POSY, Shoshana L.; SISTLA, Ramesh Kumar; HEGDE, Subramaya; RAMACHANDRA, Anupama; (425 pag.)WO2018/5586; (2018); A1;,
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16066-84-5, name is tert-Butyl methylcarbamate, 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. 16066-84-5

A. Methyl-oxiranylmethyl-carbamic acid tert-butyl ester. To a solution of Methyl-carbamic acid tert-butyl ester (1 g, 7.62 mmol) in anhydrous DMF (25 mL) cooled to 0 C. was added sodium hydride (60% dispersion in mineral oil, 0.33 g, 8.38 mmol). After stirring the solution at 0 C. for 30 minutes and 1 hour at room temperature, a solution of 2-Bromomethyl-oxirane (1.04 g, 7.62 mmol) in DMF (2.5 mL) was added dropwise. After stirring the solution at room temperature for 24 hours, the reaction mixture was diluted with ethyl acetate and quenched with water and brine. The ethyl acetate layer was then successively washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield an oil. The oil was purified via flash chromatography (10% ethyl acetate in dichloromethane) to yield the title compound as a clear oil (0.88 g, 62%). 1H NMR (400 MHz, CDCl3) delta 3.78-3.75 (m, 0.5H), 3.56-3.50 (m, 0.5H), 3.21-3.07 (m, 2H), 2.94 (s, 3H), 2.79-2.77 (m, 1H), 2.53-2.51 (m, 1H), 1.47 (s, 9H).

Statistics shows that 16066-84-5 is playing an increasingly important role. we look forward to future research findings about tert-Butyl methylcarbamate.

Reference:
Patent; BIGNAN, Gilles; Gaul, Micheal; Xu, Guozhang; Zhao, Bao-Ping; US2011/200586; (2011); A1;,
Amide – Wikipedia,
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121492-06-6, 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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, This compound has unique chemical properties. The synthetic route is as follows.

Step 3 [0211] To a stirred solution of N-Boc-N-methyl ethylenediamine (1.39 g, 8.0 mmol) and DIEA (1.05 g, 8.1 mmol) in dry DCM (50 mL) at 0C was added a solution ofp- nitrobenzylchloroformate (1.75 g, 8.1 mmol) in dry DCM (10 mL) dropwise over 5- 10 minutes. The reaction mixture was stirred at this temperature for 30 minutes and then allowed to warm to room temperature, and stirred overnight (monitored by TLC). The reaction mixture was then washed with 1M aq. NaHC03 solution, water, and brine. The organic layer was dried over Na2S04, concentrated , and the remaining residue was purified by flash chromatography to give the desired N-Boc-N’-PNB protected intermediate in 73% yield.

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; FOB SYNTHESIS; WO2005/123066; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 90-16-4, name is Benzo[d][1,2,3]triazin-4(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., 90-16-4

0.294 g (2.0 mmol) of benzo[d][1,2,3]triazin-4(3H)-one,0.418 g (2.0 mmol) of 5-(2-chloroethyl)-3-phenyl-1,2,4-oxadiazole,0.276 g (2.0 mmol) of potassium carbonate was added to 20 ml of acetone, and the temperature was raised to reflux.TLC tracks the progress of the reaction. After the reaction is completed, the solvent is distilled off under reduced pressure.50 ml of saturated sodium chloride was added to the residue, and extracted with dichloromethane (50 ml ¡Á 2).The organic phase is dried over anhydrous sodium sulfate, concentrated and purified by column chromatography.A white solid of 0.49 g was obtained in a yield of 77%.

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; East China University of Science and Technology; Xu Xiaoyong; Li Zhong; Chen Xiulei; Li Wei; Jia Haowu; Cao Xiaofeng; Shao Xusheng; Xu Zhiping; (70 pag.)CN108276352; (2018); A;,
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90-16-4, A common compound: 90-16-4, name is Benzo[d][1,2,3]triazin-4(3H)-one, 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.

General procedure: A stirring suspension of 1,2,3-benzotriazin-4-one (6 mmol), 1,2-dibromoethane (18 mmol), potassium carbonate (12 mmol), and acetone (50 ml) was refluxed for 5-8 h and then cooled to room temperature. The reaction mixture was evaporated under reduced pressure, and water (100 mL) was added to the residue, which was extracted with CH2Cl2 (50 mL ¡Á 2). The organic layer was dried over anhydrous Na2SO4, concentrated, and purified with flash chromatography on silica gel, eluting with petroleum ether (60-90C)/EtOAc to afford compound 5 in yield of 62%.

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, Benzo[d][1,2,3]triazin-4(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Xiulei; Jia, Haowu; Li, Zhong; Xu, Xiaoyong; Chinese Chemical Letters; vol. 30; 6; (2019); p. 1207 – 1213;,
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