Tag: M.W=100-200

3984-14-3, 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. 3984-14-3, name is N,N-Dimethylsulfamide, This compound has unique chemical properties. The synthetic route is as follows.

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 was 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).An alternative method for the preparation of 1H-indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]- is described below.To a 1 L four necked round bottom flask equipped with a mechanical stirrer, a temperature controller, a N2 inlet, and a condenser, under N2, was added 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (102.0 g, 0.259 mol) and dry THF (300 mL). After stirring for 10 min, CDI (50.3 g, 0.31 mol) was added portion wise. The reaction mixture was then heated to 50 oC. for 2 h. After cooling to 30 oC., N,N-dimethylaminosulfonamide (41.7 g, 0.336 mol) was added in one portion followed by addition of DBU (54.1 mL, 0.362 mol) drop wise over a period of 1 h. The reaction mixture was then stirred at rt for 20 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 1 N HCl (1:1, 2 L). The organic layer was separated and the aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were washed with brine (1.5 L) and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude product (111.0 g). The crude product was suspended in EtOAc (400 mL) at 60 oC. To the suspension was added heptane (2 L) slowly. The resulting suspension was stirred and cooled to 0 oC. It was then filtered. The filter cake was rinsed with small amount of heptane and house vacuum air dried for 2 days. The product was collected as a white solid (92.0 g, 83%). 1H NMR (MeOD, 300 MHz) delta 7.89 (s, H), 7.77 (d, J=8.4 Hz, 1H), 7.55 (dd, J=8.4 and 1.8 Hz, 1H), 3.01 (s, 6H), 2.73-2.95 (m, 1H), 1.81-2.05 (m, 8H), 1.39-1.50 (m, 2H); m/z 429 (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; Bristol-Myers Squibb Company; US2009/130056; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1118-69-0, name is N-Isopropylacetamide, belongs to amides-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 1118-69-0, 1118-69-0

Preparation of Zr(LMeJPr)4 (28). A 100 ml_ Schlenk flask, fitted with a reflux condenser, was charged with tetrakis(dimethylamido)zirconium (0.200 g, 0.748 mmol) and toluene (10 ml_). A solution of LMe iotaPrH (0.302 g, 2.99 mmol) in toluene (10 ml_) was added slowly and the resultant mixture was refluxed for 3 h. Upon cooling to room temperature, the volatile components were removed under reduced pressure and sublimation of the crude solid at 110 C/0.05 Torr afforded 28 as colorless crystals (0.188 g, 51 %): mp 206-209 0C.

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-Isopropylacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WAYNE STATE UNIVERSITY; WINTER, Charles, H.; KNISLEY, Thomas, Joseph; KARUNARATHNE, Panditha Koralalage, Don Mahesh Chinthaka; WO2010/132871; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6331-71-1, name is 4-Amino-N,N-dimethylbenzamide, belongs to amides-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 6331-71-1, 6331-71-1

EXAMPLE 22 A mixture of 9 parts of 4-amino-N,N-dimethylbenzamide, 137 parts of concentrated hydrochloric acid and 90 parts of water was stirred at room temperature. 21.6 Parts of a hydrogen peroxide solution 30% in water were added and the whole was stirred for 4 hours at room temperature. The product was extracted three times with dichloromethane. The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2′-oxybispropane. The product was filtered off and dried, yielding 5.78 parts (46%) of 4-amino-3,5-dichloro-N,N-dimethylbenzamide; mp. 134.2 C. (int. 110).

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-N,N-dimethylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica N.V.; US4880808; (1989); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

92136-39-5, 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 92136-39-5 as follows.

A solution of copper cyanide (1.1Sg, 12.9 mmol) in THF (30 mL) at ?78 C. was treated slowly with n-butyllithium (16.9 mL, 27.1 mmol), stirred for 15 minutes at ?78 C., treated with tributyltin hydride (7.88 g, 7.30 mL, 27.1 mmol) over a period of 5 minutes, stirred for 15 minutes, treated with tert-butyl 2-propynylcarbamate (2.00 g, 12.9 mmol) in tetrahydrofuran (7 mL), stirred at ?780C for 1 hour, and treated with a 9:1 aqueous solution of ammonium chloride:ammonium hydroxide (250 mL) and dichloromethane (200 mL). The suspension was filtered through a short pad of diatomaceous earth (Celite). The organic phase of the filtrate was washed with brine and concentrated. The residue was purified on silica gel using 1-2% ethyl acetate/heptane to provide the desired product (3.66 g, 63%). 1H NMR (400 MHz, CDCl3) ? 6.08 (dt, B part of an AB system, J=19.3 Hz, 1.3 Hz, 1H); 5.93 (dt, A part of an AB system, J=19.3 Hz, 4.8 Hz, 1H), 4.59 (br s, 1H), 3.78 (br s, 2H), 1.45 (s, 9H), 1.32-1.26, (m, 12H), 0.90-0.85 (m, 15H).

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

Reference:
Patent; Betschmann, Patrick; Burchat, Andrew; Calderwood, David; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin; Hrnciar, Peter; Michaelides, Michael; Rafferty, Paul; US2005/20619; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 1943-79-9, name is Phenyl methylcarbamate, 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. 1943-79-9

5-((2-amino-4-pyridyl)oxy)-3-chloro-1H-1-indole (4.0 g, 15 mmol, CAS No. 417721-98-3) which was described in WO 02/32872 was dissolved in N,N-dimethylformamide (20 ml); sodium hydride (0.68 g, 60% in oil) and phenyl N-methylcarbamate (2.6 g, the product of Production example 2-1) were added thereto; and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane: ethyl acetate = 1: 2) to yield the title compound as a colorless amorphous solid(1.5 g). 1H-NMR Spectrum (DMSO-d6) delta (ppm): 2.83 (3H, d, J=4.0 Hz), 5.78 (1H, d, J=2.0 Hz), 5.88 (2H, brs), 6.14 (1H, dd, J=2.0, 5.8 Hz), 7.14 (1H, dd, J=2.4, 9.0 Hz), 7.23 (1H, d, J=2.4 Hz), 7.78 (1H, d, J=5.8 Hz), 8.08 (1H, s), 8.19 (1H, m), 8.32 (1H, d, J=9.0 Hz).

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 1943-79-9.

Reference:
Patent; Eisai Co., Ltd.; EP1522540; (2005); 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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, A new synthetic method of this compound is introduced below., 67442-07-3

Benzylmagnesium chloride (1.0 M in diethyl ether, 50.0 mL) was treated with 2-chloro-N-methoxy-N-methylacetamide (5.16 g, 37.5 mmol) in tetrahydrofuran (200 mL) at -78¡ã C. drop wise. The reaction was allowed to warm slowly to room temperature overnight and quenched with 1N hydrochloric acid. The layers were separated and the organic phase dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel; elution with hexanes) to provide the title. 1H NMR (300 MHz, DMSO-d6) delta 3.87 (s, 2H), 4.62 (s, 2H), 7.25 (m, 5H); MS (DCI/NH3) m/z 186 (M+NH4)+.

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; Kolasa, Teodzyj; Patel, Meena; Mortell, Kathleen H.; Matulenko, Mark A.; Hakeem, Ahmed A.; Bhatia, Pramila A.; Wang, Xueqing; Daanen, Jerome F.; Latshaw, Steven P.; Stewart, Andrew O.; US2005/176727; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, molecular formula is C4H8ClNO2, 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. 67442-07-3

To an oven dried, N2-flushed 100 mL round bottom flask was added 5-cyclohexyl-5-methylimidazolidine-2,4-dione (Example 2.47d) (6.77 g, 32.9 mmol), K2CO3 (6.80 g, 49.3 mmol) 32 mL of anhydrous DMF and commercially available 2-chloro-N-methoxy-N-methylacetamide (4.74 g, 34.5 mmol). The reaction was stirred at 50¡ã C. for 12 h. The reaction was cooled and 70 mL water was added with stirring. The precipitate was filtered and dried to afford 8.9 g (92percent) of 2-(4-cyclohexyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-N-methoxy-N-methylacetamide as a white solid. (0741) To an oven dried, N2-flushed 100 mL round bottom flask was added 2-(4-cyclohexyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-N-methoxy-N-methylacetamide (8.90 g, 29.9 mmol), Cs2CO3 (13.65 g, 41.9 mmol), 30 mL DMF and methyl iodide (2 mL, 31.4 mmol). The reaction was stirred for 24 hours and 60 mL water was added. The mixture was extracted with ether (3¡Á50 mL). The combined organic layers were washed with water (1¡Á100 mL), brine and dried with Na2SO4. The solvent was evaporated, and the residue was purified by column chromatography utilizing a Silicycle column (120 g) and elution with 20-70percent ethyl acetate/hexane to afford 8.2 g (88percent) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) delta 4.28 (s, 2H), 3.73 (s, 3H), 3.10 (s, 3H), 2.78 (s 3H), 1.79-1.49 (m, 6H), 1.39-1.25 (m, 4H), 1.23-0.82 (m, 4H); MS 312 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 67442-07-3, its application will become more common.

Reference:
Patent; SENOMYX, INC.; Chumakova, Lyudmyla; Patron, Andrew; Priest, Chad; Karanewsky, Donald; Kimmich, Rachel; Boren, Brant Clayton; Hammaker, Jeffrey Robert; Chumakov, Volodymyr; Zhao, Wen; Noncovich, Alain; Ung, Jane; (146 pag.)US2015/376136; (2015); 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. 630-22-8, name is 2,2-Dimethylpropanethioamide, A new synthetic method of this compound is introduced below., 630-22-8

To a solution of N-(3-(2-bromo-2-(2-(methylthio)pyrimidin-4-yl)acetyl)-2- chloro-5-fluorophenyl)-pivalamide (AT, 489 mg, 1.03 mmol) in DMA (4.7 mL) under Ar at rt was added 2,2-dimethylpropanethioamide (131 mg, 1.12 mmol). The reaction mixture was stirred at rt for 1 h, and then heated to and maintained at 80 C for 3 h. The reaction was judged complete by LCMS. The reaction mixture was diluted with water and twice extracted with EtOAc. The organic phases were combined, washed with brine, dried (Na2S04), and concentrated. The resulting residue was adsorbed onto silica gel and purified by flash chromatography on silica gel using an EtOAc :heptanes (0-15%) elution gradient to furnish N-(3 -(2 -tert-butyl-5 -(2-(methylthio)pyrimidin-4-yl)thiazol-4-yl)-2-chloro-5 – fluorophenyl)pivalamide (175 mg, 0.36 mmol, 38 %) as a white foam: LCMS (m/z): 493.1 (MH+), tR = 1.42 min.

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; NOVARTIS AG; MADERA, Ann Marie; POON, Daniel; SMITH, Aaron; WO2011/161216; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

2895-21-8, 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 2895-21-8 as follows.

EXAMPLE 1 The compound N-isopropyl-alpha-chloroacetamide (2.71 g; 0.02 mole) and benzyltriethylammonium chloride (0.09 g) were dissolved in methylene chloride (50 ml) in a 100 ml flask. A 50% by weight sodium hydroxide solution (16 g) was added to the mixture, and the mixture was stirred vigorously at 40 C. for three days. Thereafter, the organic phase was separated, dried and evaporated. The residue of the evaporation (found to be four parts product per part starting material) was recrystallized from ethyl alcohol to yield 0.7 g (36%) of 1,4-diisopropyl-2,5-diketopiperazine. All spectral data were consistent with this structure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2895-21-8, and friends who are interested can also refer to it.

Reference:
Patent; Monsanto Company; US4694082; (1987); A;,
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 90-16-4 as follows. 90-16-4

General procedure: Propargyl bromide (1.2 mmol) was added to a solution of 1aa or 1bb or 1cc (1.0 mmol) and K2CO3 (3.0 mmol) in CH3CN (25 mL) under a nitrogen atmosphere. The mixture was stirred at room temperature for 3 h. After completion of the reaction (confirmed by TLC), the mixture was diluted with ice-water (60 mL) and extracted with EtOAc(3¡Á15 mL). The organic layers were collected, combined, dried over anhydrous Na2SO4, filtered and concentrated under low vacuum. The residue was purified by column chromatography using hexane- EtOAc as eluent to afford the title compound.

According to the analysis of related databases, 90-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Reddy, Gangireddy Sujeevan; Snehalatha, Ampalam Venkata; Edwin, Rebecca Kristina; Hossain, Kazi Amirul; Giliyaru, Varadaraj Bhat; Hariharapura, Raghu Chandrashekhar; Gautham Shenoy; Misra, Parimal; Pal, Manojit; Bioorganic Chemistry; vol. 91; (2019);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics