Amides-buliding-blocks

These common heterocyclic compound, 27366-72-9, name is 2-(Dimethylamino)ethanethioamide hydrochloride, 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. 27366-72-9

EXAMPLE 9 Preparation of N-methyl-N’-2-([2-(dimethylaminomethyl)-5-methyl-4-thiazolyl]methylthio)ethyl 2-nitro-1,1-ethenediamine Following the procedure of Example 1, a reaction mixture containing 33.88 g. of ethyl 2-oxo-3-bromobutyrate [prepared by the procedure of Siefert et al., Helv. Chim. Acta, 33 725 (1950)], 21.52 g. of dimethylaminothioacetamide hydrochloride and 100 ml. of anhydrous ethanol was stirred and heated to refluxing temperature for about 2.5 hours. The reaction mixture was allowed to remain at room temperature overnight after which time it was concentrated by evaporation in vacuo. 100 ml. of an ice-water mixture was added to the resulting residue and the aqueous layer extracted with ethyl acetate. The ethyl acetate layer was discarded. The aqueous layer was cooled and then made basic (pH=11) with 2 N aqueous sodium hydroxide. The resulting alkaline layer was extracted several times with an equal volume of ethyl acetate and the ethyl acetate extracts were combined. The combined extracts were washed with water, with saturated aqueous sodium chloride, and were then dried. Concentration in vacuo provided a reddish oil comprising ethyl 2-(dimethylaminomethyl)-5-methyl-4-thiazolecarboxylate. Yield=21.2 g. (57%)

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 27366-72-9.

Reference:
Patent; Eli Lilly and Company; US4375547; (1983); A;,
Amide – Wikipedia,
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749927-69-3, The chemical industry reduces the impact on the environment during synthesis 749927-69-3, name is 4-Bromo-2-fluoro-N-methylbenzamide, I believe this compound will play a more active role in future production and life.

The bromobenzamide A-2 (10 g, 43.1 mmol), aminoisobutyric acid B-l (6.7 g, 64.6 mmol, 1.5 equiv), K2C03 (15 g, 2.5 equiv), 99% CuCl (0.8 g, 8.1 mmol, 0.2 equiv), DMF (60 mL, 6 vol) and water (1.8 mL) were added to the flask and the reaction slurry was heated to 30 C. 2-Acetylcyclohexanone (1.14 mL, 8.1 mmol, 0.2 equiv) was added to the reaction slurry followed by stirring at 105 C under nitrogen for 12-14 h. HPLC analysis showed 96.6% conversion to the desired product. The reaction mixture was then cooled to RT and extracted with water (120 mL) and IP Ac (60 mL). The lower aqueous layer was re-extracted with IP Ac (60 mL) and acidified with 180 mL of 1M citric acid to a pH of 4.0. The product began to crystallize at RT and the batch was further cooled to 5-7 C, filtered, washed with water (40 mL) and dried under vacuum at 50 C for 12 h. The reaction yielded 8.3 g of product C-1 (75.4% yield) as a tan solid with HPLC purity of 99.6%.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2-fluoro-N-methylbenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MEDIVATION PROSTATE THERAPEUTICS, INC.; JAIN, Rajendra, Parasmal; ANGELAUD, Remy; THOMPSON, Andrew; LAMBERSON, Carol; GREENFIELD, Scott; WO2011/106570; (2011); A1;,
Amide – Wikipedia,
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563-83-7, The chemical industry reduces the impact on the environment during synthesis 563-83-7, name is Isobutyramide, I believe this compound will play a more active role in future production and life.

A solution of 2-methylpropanamiotade (6 53 g, 75 0 mmol) and 2,4-biotas(4- methoxyphenyl)-1 ,3-diotathiotaa-2,4-diotaphosphetane-2,4-diotasulfiotade (15 17 g, 37 51 mmol) in THF (100 mL) was heated to reflux for 4 h The reaction mixture was then cooled to rt and poured into saturated aqueous NaHCO3 (200 mL) The mixture was extracted with ether (4 x 100 mL) The organic fractions were combined, dried over Na2SO4, filtered, and concentrated Purification by flash column chromatography (20% EtOAc hexanes) afforded 4 77 g (62%) of the title compound of Step A 1H-NMR (400 MHz, CDCI3) delta 7 63 (brs, 1 H), 6 90 (brs, 1 H), 2 88 (m, 1 H), and 1 27 (d, 6H, J = 6 8 Hz)

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

Reference:
Patent; GLAXOSMITHKLINE LLC; ADJABENG, George; BAUM, Erich; BIFULCO, Neil; DAVIS-WARD, Ronda, G.; DICKERSON, Scott, Howard; DONALDSON, Kelly, Horne; HORNBERGER, Keith; PETROV, Kimberly; RHEAULT, Tara, Renae; SAMMOND, Douglas, McCord; SCHAAF, Gregory, M.; STELLWAGEN, John; UEHLING, David, Edward; WATERSON, Alex, Gregory; WO2010/104899; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, 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. 239074-29-4

To a mixture of 7-fluoro-8-hydroxy-l-methyl-2(lH)-quinoxalinone (150 mg), 1,1- dimethylethyl [tralpha/?5-4-(hydroxymethyl)cyclohexyl] carbamate (142 mg, 0.618 mmol, for a preparation see Example l(g)) and triphenylphosphine (195 mg, 0.742 mmol) in THF (10 mL) was added DIAD (0.144 mL, 0.742 mmol) and the mixture was stirred at rt for 1 h then triphenylphosphine (195 mg, 0.742 mmol) and DIAD (0.144 mL, 0.742 mmol) were added and the reaction was stirred at rt overnight. The solvent was evaporated and the residue was purified using silica chromatography (0-20%CH3CN/DCM) to afford the title compound (272 mg) which was used in the next step without further purification. MS (ES+) m/z 423 [MNH4+].

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 239074-29-4.

Reference:
Patent; GLAXO GROUP LIMITED; JONES, Graham, Elgin; MARKWELL, Roger, Edward; HENNESSY, Alan Joseph; MILES, Timothy; PEARSON, Neil David; WO2010/45987; (2010); A1;,
Amide – Wikipedia,
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1565-17-9, 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. 1565-17-9, name is 4-Acetylbenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: An amountof acetic acid glacial was added to a mixture of acetophenoneand phenyl hydrazine derivatives in 20 ml ethanol (EtOH),and the reaction was reBuxed overnight at 70C. Ethanol wasremoved under reduced pressure and the produced solidproduct was used without further puri7cation for pyrazolesynthesis.

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

Reference:
Article; Assali, Mohyeddin; Abualhasan, Murad; Sawaftah, Hadeel; Hawash, Mohammed; Mousa, Ahmed; Journal of Chemistry; vol. 2020; (2020);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

239074-29-4, 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 239074-29-4 as follows.

To a solution of tert-butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate (0.84 g, 3.65 mmol) in THF (15 mL) was added No.23 triphenylphosphine (1.43 g, 5.45 mmol) and No.23 4,6-dichloropyrimidin-5-ol (0.68 g, 3.65 mmol). To the mixture was added No.23 diisopropylazodicarboxylate (1.47 g, 7.27 mmol) at 0C., the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=40:1 as eluent) to afford the tert-butyl (trans-4-(((4,6-dichloropyrimidin-5-yl)oxy)methyl)cyclohexyl)carbamate as colorless oil (0.45 g, 33% yield). LC/MS APCI: Calculated 375.11; Observed m/z [M-99 (boc)]+ 276.1. 1H-NMR 400 MHz, DMSO-d6: delta 8.68 (s, 1H), 6.75 (d, J=7.60 Hz, 1H), 3.94 (d, J=6.00 Hz, 2H), 3.16-3.14 (m, 1H), 1.89-1.79 (m, 4H), 1.73-1.71 (m, 1H), 1.38 (s, 9H), 1.19-1.16 (m, 4H).

According to the analysis of related databases, 239074-29-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Arrien Pharmaceuticals LLC; Vankayalapati, Hariprasad; US2020/131154; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

631-58-3,Some common heterocyclic compound, 631-58-3, name is Propanethioamide, molecular formula is C3H7NS, 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.

EXAMPLE 9 A mixture of 3.6 parts of propanethioamide, 8.6 parts of 2-bromo-1-(4-hydroxyphenyl)ethanone and 79 parts of ethanol was stirred for 7 hours at reflux temperature. The reaction mixture was concentrated to 1/4 of its volume and 2,2′-oxybispropane was added to the residue. The precipitate was filtered off and taken up in water. After basifying with NH4 OH, the product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 3.3 parts (40.2%) of 4-(2-ethyl-4-thiazolyl)-phenol (interm. 17).

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

Reference:
Patent; Janssen Pharmaceutica N.V.; US5100893; (1992); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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

6292-59-7, Adding a certain compound to certain chemical reactions, such as: 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, 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 6292-59-7.

Example 3: Preparation of propionic acid 2-[6-(4-tert-butyl-benzenesulfonylamino)-5- (2-methoxy-phenoxy)-[2, 2′] bipyrimidinyl-4-yloxy]-ethyl ester compound of formula IV.A mixture of 4-tert butyl benzene sulfonamide (49.5g, 1eq), Potassium phosphate (123.8g, 2.5eq) dimethyl acetamide (500ml, 5vol) was heated to 40¡ãC and maintained for 30-60 minutes. Propionic acid 2-[6-chloro-5-(2-methoxy-phenoxy)-[2,2′] bipyrimidinyl-4-yloxy]-ethyl ester of formula V (100g, 1 eq) was added to the reaction mixture and the reaction mass was heated to 90¡ãC for 24-28 hours. Filtered the inorganic solid and washed the solid with dimethyl acetamide (100ml, 1vol). To the mixture of water (2.5L, 25vol) and concentrated hydrochloric acid (150ml, 1.5Vol) was added the filtrate at 0-5¡ãC. Maintained the stirring for 1-2 hours at 0-5¡ãC .Filtered the solid and washed with water (500ml, 5vol). Dissolved the wet cake in DCM (500ml, 5Vol) and added to a mixture of water (700ml,7vol) and concentrated hydrochloric acid (75ml, 0.75vol) at 10-15¡ãC.Stirred, separated the DCM layer and repeated the washing with mixture of water (700ml, 7vol) and concentrated hydrochloric acid (75ml, 0.75vol) at 10-15¡ãC. Separated the DCM layer and washed with water (500ml, 5vol). Distilled DCM under vacuum at 35-40¡ãC to get title compound (yield 110g, HPLC purity- 85percent).

According to the analysis of related databases, 6292-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MATRIX LABORATORIES LTD; GORE, Vinayak; BINDU, Manojkumar; SHINDE, Dattatraya; KOKANE, Dattatrey; GHRAT, Sushant; DANDALA, Ramesh; WO2012/56468; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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,
Amide – an overview | ScienceDirect Topics