Tag: M.W=100-200

915087-25-1, A common compound: 915087-25-1, name is 4-Amino-2-fluoro-N-methylbenzamide, 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.

Synthesis of 4-(l-Cyano-cyclobutylamino)-2-fluoro-N-methyl-benzamide 6a.[00195] TMS-CN (29.7g, 300mmol) was added to a mixture of N-methyl-2-fluoro -4- aminobenzamide 4a (16.8g, lOOmmol) and cyclobutanone (14g, 200mmol) in 90%) acetic acid (200mL). The reaction mixture was stirred at 80C for 24h. The mixture was cooled and diluted with water (200mL). The suspension was extracted with ethyl acetate (3x200mL). Combined organic layers were washed with brine (4xl00mL), dried (MgS04) and concentrated in vacuo to dryness. The residue was triturated with a mixed solvent of hexanes and ethylether (20mL-20mL) to remove cyclobutanone cyanohydrin. The solid was collected by filtration, affording the title compound 6a (20g, 84% yield). MS(ES-API Negative): 246 (M-H)-. 1H NMR (CDC13, 500MHz): delta 7.92 (1H, dd, J=8.4, 8.4 Hz), 6.76 (1H, q, J=4.3Hz), 6.48 (1H, dd, J=8.3, 1.9Hz), 6.29 (1H, dd, J=14.3, 1.9Hz), 4.72 (1H, br s), 2.97 (3H, d, J=4.4Hz), 2.85-2.75 (2H, m), 2.4-2.35 (2H, m), 2.3-2.15 (1H, m), 1.95-1.85 (1H, m).

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-Amino-2-fluoro-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TONG, Youzhi; WO2011/29392; (2011); A1;,
Amide – Wikipedia,
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3984-14-3, 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 3984-14-3 as follows.

EXAMPLE 19; (compound 64) (IC50=B*, EC50=E*)IS-cyclohexyl-N-zetadimethylaminosulfonylJ-YH-indoloftJ-aJftJbenzazepine- 10-carboxamide. A mixture of Example 15 (50 mg, 0.14 mmol), N5N- dimethylsulfamide (21 mg, 0.17 mmol), 4-(dimethylamino)pyridine (17 mg, 0.14 mmol), and l-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (40 mg, 0.21 mmol) in dichloromethane (1 mL) and DMF (1 mL) was stirred for 18 hours at 22 C. The mixture was poured into ethyl acetate and dilute aqueous acetic acid. The ethyl acetate layer was washed (water, brine), dried (Na2SO4), filtered, and concentrated. The residue was crystallized from ethyl acetate to provide the desired product (17 mg, 26% yield) as pale yellow crystals. ESI-MS m/z 358 (MH+); 1H NMR (300 MHz5 CDCl3) delta 1.20-2.30 (m, 10H), 2.81 (m, IH), 3.05 (s, 3H), 3.47 (m, 2H), 4.11 (m, IH,) 4.89 (s, IH), ,6.27 (m, IH), 6.80 (d, J=10.61 Hz, IH), 7.38 (m, 4H), 7.51 (m, IH), 7.89 (d, J=8.42 Hz, IH), 8.02 (s, IH), 8.75 (s, IH).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/92000; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

2430-27-5, name is 2-Propylpentanamide, 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. 2430-27-5

General procedure: To a solution of the appropriate drug (D1-CONH2,1.00 mmol) in CH2Cl2 (5 mL) at 0 – 5 oC wasadded oxalyl chloride (1.30 mmol) drop-wise and refluxed for 24 h. The reactionmixture was concentrated and the residue was dissolved in DCE (5 mL). To thiswas added a solution of 11 (2.00mmol) in DCE (5 mL) and stirred for 24 h. The reaction mixture was concentratedand the residue was partitioned between EtOAc (20mL) and water (10 mL). Theorganic layer was washed with water and brine (10 mL each), dried (Na2SO4),concentrated and purified by silica gel column chromatography to afford thetitle compounds

Statistics shows that 2430-27-5 is playing an increasingly important role. we look forward to future research findings about 2-Propylpentanamide.

Reference:
Article; Jain, Arun K.; Gund, Machhindra G.; Desai, Dattatraya C.; Borhade, Namdev; Senthilkumar, Subrayan P.; Dhiman, Mini; Mangu, Naveen K.; Mali, Sunil V.; Dubash, Nauzer P.; Halder, Somnath; Satyam, Apparao; Bioorganic Chemistry; vol. 49; (2013); p. 40 – 48;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

16982-21-1, A common compound: 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate, 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.

[00144] Synthesis of ethyl 2-amino-2-hydrazonoacetate (6): Ethyl 2-amino-2- thioxoacetate (5) (5g, 37.5 mmol) was dissolved in ethanol and cooled to 0 C. Hydrazine in THF (1M, 37.5 mmol) was added dropwise and stirred at ambient temperature for lh. The reaction mixture was concentrated, white flakes of ethyl 2- amino-2-hydrazonoacetate 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, Ethyl 2-amino-2-thioxoacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DODD, Dharmpal, S.; MUSSARI, Christopher, P.; BHIDE, Rajeev, S.; NAIR, Satheesh Kesavan; PAIDI, Venkatram Reddy; KUMAR, Sreekantha Ratna; BANERJEE, Abhisek; SISTLA, Ramesh; PITTS, William, J.; HYNES, John; WO2013/106614; (2013); A1;,
Amide – Wikipedia,
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1882-71-9, 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. 1882-71-9, name is 2-Amino-5-methoxybenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 29: (4-Chloro-phenyl)-{4-[4-hydroxy-l-(6-methoxy-2-trifluoromethyl- quinazolin-4-yl)-pyrrolidin-3-yl]-piperazin-l-yl}-methanone[00236] Step 1 : 6-methoxy -2-trifluoromethyl-3H-quinazolin-4-one[00237] To 2.99 mmoles of 2-amino-5-methoxy anthranilic acid in 1OmL acetonitrile, add 14.9 mmoles of pyridine. The reaction mixture was cooled in ice and then 8.97 mmoles of trifluoroacetic EPO anhydride was added to the reaction mixture and it was slowly warmed to room temperature and allowed to stir for 2 hours. This reaction mixture was added to an ice cooled suspension of 11.96 mmoles ammonium carbonate in 5mL acetonitrile and it was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated to a thick oil, 1OmL acetic acid was added to the residue and it was heated at 118-1200C for 2.5-3 hours. The reaction mixture was concentrated and then a 1:1 soln of ethanol-water was added, the white solid obtained was filtered and washed with fresh cold ethanol-water and vaccum dried to yield the title compound in 74 percent yield. LC-MS: m/z= 245 (M+ +1)

The synthetic route of 1882-71-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2006/71875; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 76114-73-3, name is Prop-2-yn-1-yl butylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 76114-73-3

EXAMPLE 1; [0050] A reactor was charged with 330 g of water which was then cooled to a temperature of 0-8 C. [0051] To the cooled water, while stirring was added 3.4 grams of a nonionic surfactant agent Merpol HCS and 16.85 g of butyl propynyl carbamate while maintaining the temperature between 0-8 C. [0052] The reactor was further charged with 8.85 g of a 50% aqueous solution of sodium hydroxide and 16.28 grams of sodium iodide which had been previously dissolved in 50 g of water. The temperature was maintained between 5-8 C. [0053] The reactor with strong agitation was slowly charged with 70.2 g of a 13.6% solution of sodium hypochlorite while maintaining the reaction mass at a temperature of between 6 and 11 C. [0054] The temperature was allowed to ramp up slightly to 15-20 C. and the reaction mass was agitated for 90 minutes. The reaction mass was then slowly heated to a temperature of 35-40 C. The ramping up of the temperature was effected at a rate of 0.25 to 0.75 C. per minute. [0055] With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then ramped up to 55 to 59 C. at a rate of 0.25 to 0.75 C. per minute. [0056] When a temperature reached a range of 55-59 C. cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30 C., at a ramp down rate of 0.33-0.75 C. per minute. [0057] The reaction mass was then agitated for 10 minutes and then the reaction mass was filtered. The filtration cake was washed twice with 100 ml of water. The cake was then dried at 35 C. to a constant weight. The reaction achieved a yield of 93.5% of IPBC which assayed at 98.7% IPBC.; A reactor was charged with 1400 gal of water which was then cooled to a temperature of 0-8 C. [0060] To the cooled water, while stirring was added to 87 pounds of a nonionic surfactant agent Merpol HCS and 429 pounds of butyl propynyl carbamate while maintaining the temperature between 0-8 C. [0061] The reactor was further charged with 214 pounds of a 50% aqueous solution of sodium hydroxide and 853 pounds of 50% sodium iodide solution. The temperature was maintained between 5-8 C. [0062] The reactor with strong agitation was slowly charged with 1780 pounds of a 13.6% solution of sodium of sodium hypochlorite while maintaining the reaction mass at a temperature of between 6 and 11 C. [0063] The temperature was allowed to ramp up slightly to 15-20 C. and the reaction mass was agitated for 90 minutes. The reaction mass was then slowly heated to a temperature of 35-40 C. The ramping up of the temperature was effected at a rate of 0.25 to 0.75 C. per minute. [0064] With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then tamped up to 55 to 59 C. at a rate of 0.25 to 0.75 C. per minute. [0065] With agitation the pH of the reaction mass was then adjusted to 6.9 with acetic acid. The pH reaction mass was then adjusted to 6.6 with sodium bisulfite. The temperature was then ramped up to 55 to 59 C. at a rate of 0.25 to 0.75 C. per minute. [0066] When a temperature reached a range of 55-59 C., cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30 C., at a ramp down rate of 33-75 C. per minute. [0067] When a temperature reached a range of 55-59 C., cooling was applied to the reaction mass to ramp the temperature of the reaction mass down to 25-30 C., at a ramp down rate of 33-75 C. per minute. [0068] The reaction mass was then agitated and then the reaction mass was centrifuged with water for 10 minutes. The cake was washed. The cake was then dried at 30-45 C. to a constant weight. The reaction achieved a yield of 93.2% of IPBC which assayed at 98.7% IPBC.

The synthetic route of 76114-73-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schneider, David J.; Schneider, Charles A.; Jones, Kurt A.; Heineke, Martin S.; US2005/33083; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 3984-14-3, name is N,N-Dimethylsulfamide, 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 3984-14-3. 3984-14-3

2-Bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-1H-indole-6-carboxamide;. 1,1′-Carbonyldiimidazole (1.17 g, 7.2 mmol) was added to a stirred solution of 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (2.03 g, 6.3 mmol) in THF (6 mL) at 22 C. The evolution of CO2 was instantaneous and when it slowed the solution was heated at 50 C. for 1 hr and then cooled to 22 C. N,N-Dimethylsulfamide (0.94 g, 7.56 mmol) was added followed by the dropwise addition of a solution of DBU (1.34 g, 8.8 mmol) in THF (4 mL). Stirring was continued for 24 hr. The mixture was partitioned between ethyl acetate and dilute HCl. The ethyl acetate layer washed with water followed by brine and dried over Na2SO4. The extract was concentrated to dryness to leave the title product as a pale yellow friable foam, (2.0 g, 74%, >90% purity, estimated from NMR). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.28-1.49 (m, 3H) 1.59-2.04 (m, 7H) 2.74-2.82 (m, 1H) 2.88 (s, 6H) 7.57 (dd, J=8.42, 1.46 Hz, 1H) 7.74 (d, J=8.78 Hz, 1H) 7.91 (s, 1H) 11.71 (s, 1H) 12.08 (s, 1H).

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 N,N-Dimethylsulfamide.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/287694; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

2675-89-0, 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. 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, This compound has unique chemical properties. The synthetic route is as follows.

Step 1To an ice-cooled solution of 2-chloro-N,N-dimethyl-acetamide (10 mL, 97.5 mmol) was added POCl3 (14 mL, 149.5 mmol). The clear mixture was stirred at room temperature for 20 min. 5,6- dihydro-4H-pyrrolo[3,2,l-ij]quinoline (10.20 g, 65.0 mmol, for preparation see WO06086486A1) was added. The mixture was stirred at 80 0C for two hours. The mixture was poured on to ice (200 mL) and dichloromethane (300 mL). Aqueous sodium hydroxide was added to adjust to pH>12. The dichloromethane layer was separated, washed with water (300 mL), dried over Na2SOzI, filtered and evaporated to give a dark solid. The solid was dissolved into DCM and purified by silica gel column chromatography (eluent: 0% to 1% EtOAc in DCM). 2-Chloro- 1 -(5,6-dihydro-4H-pyrro Io [3,2,1 – ij]quinolin-l-yl)-ethanone was obtained as an off-white solid (10.82 g, 71%) after tituration with EtOAc. M.p.= 118-1 19 0C; 1H NMR (400 MHz, CDCl3) delta: 8.00 (d, J= 8.0 Hz, IH), 7.82 (s, IH), 7.23 (m, IH), 7.03 (d, J= 7.2 Hz, IH), 4.51 (s, 2H), 4.21 (t, J= 6.0 Hz, 2H), 3.01 (t, J= 6.0 Hz, 2H), 2.27 (m, 2H). LCMS: m/e 234.03 [M+H].

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; ARQULE, INC.; WO2009/2806; (2008); 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. 1882-71-9, name is 2-Amino-5-methoxybenzamide, A new synthetic method of this compound is introduced below., 1882-71-9

General procedure: To a cold (0?5 ¡ãC) stirred suspension of aminobenzamides 15a?f and 20a,b (0.016 mol) in pyridine (13 mL), 0.016 mol of the appropriate phenoxyacetyl chloride 16a?e was added over 30 min. After addition was complete, the solution was stirred for24 h and then poured onto crushed ice. The precipitate was removed by filtration, washed with water, and crystallized from the indicated solvent.

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; Raffa, Demetrio; Maggio, Benedetta; Plescia, Fabiana; Cascioferro, Stella; Raimondi, Maria Valeria; Cancemi, Gabriella; D’Anneo, Antonella; Lauricella, Marianna; Cusimano, Maria Grazia; Bai, Ruoli; Hamel, Ernest; Daidone, Giuseppe; Bioorganic and Medicinal Chemistry; vol. 23; 19; (2015); p. 6305 – 6316;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

640-61-9, 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. 640-61-9, name is N,4-Dimethylbenzenesulfonamide, A new synthetic method of this compound is introduced below.

To a solution of bromoethynylbenzene (1.4 g, 8.0 mmol) in 24 mL of anhydrous toluene in a reaction vial were added methyl phenylcarbamate (1.5 g, 9.6 mmol), K3PO4 (3.4 g, 16 mmol), copper sulfate-pentahydrate (400 mg, 16 mmol), and 1,10-phenanthroline (577 mg, 3.2 mmol). The reaction mixtures was capped under an argon atmosphere, and heated in an oil bath at 80 ?C for 15 h. The progress of the reaction was monitored using TLC analysis. Upon completion, the reaction mixture was allowed to cool to room temperature, and diluted with 15 mL of ethyl acetate. The mixture was filtered through a pad of celite, and the filtrate was concentrated in vacuo. The crude residue was purified by column chromatography with eluent of Hexane/ ethyl acetate = 19/1 to give 1.6 g of 1 in 80 % yield as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.55 (dd, J = 1.2, 8.6 Hz, 2H), 7.45-7.40 (m, 4H), 7.33-7.28 (m, 4H), 3.92 (s, 3H). 13C NMR. (100 MHz, CDCl3) delta 154.9, 139.7, 131.5, 129.1, 128.4, 128.0, 127.2, 124.8, 123.0, 83.0, 70.3, 54.5.

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:
Article; Sato, Akihiro H.; Ohashi, Kazuhiro; Iwasawa, Tetsuo; Tetrahedron Letters; vol. 54; 10; (2013); p. 1309 – 1311;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics