Author: Jessica.F

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. 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H12N2O2S

General procedure: To a cooled solution of triphosgene (1.41mmol) in THF at 0¡ãC, a mixture of primary amine (3.52mmol) and N,N-diisopropylethylamine (DIPEA, 7.04mmol) was added. The reaction mixture was stirred at the same temperature for 30min and then the other amine (3.52mmol) was added. The reaction mixture was slowly allowed to attain ambient temperature and further stirred for 8h. After the completion of the reaction, water was added to the reaction mixture and extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude mixture was subjected to column chromatography to obtain the pure compounds.

According to the analysis of related databases, 35303-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Manickam, Manoj; Jalani, Hitesh B.; Pillaiyar, Thanigaimalai; Boggu, Pulla Reddy; Sharma, Niti; Venkateswararao, Eeda; Lee, You-Jung; Jeon, Eun-Seok; Son, Min-Jeong; Woo, Sun-Hee; Jung, Sang-Hun; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1869 – 1887;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 7341-96-0, These common heterocyclic compound, 7341-96-0, name is Propiolamide, 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.

Example 2.1: Ethyl 2-{2-ethoxy-2-oxoethyl)-6-oxo-1,6-dihydropyridine-3- cartooxylate; Propiolamide (20.0 g, 289.6 mmol), diethyl 3-oxopentanedioate (87.8 g, 434.4 mmol) and sodium carbonate (24.6 g, 231.7 mmol) were mixed in water (800 mL) at 0 0C and then warmed to r.t. over 4 hours. The reaction was allowed to continue t? stir at r.t. for 3 days. The reaction was neutralized with aqueous hydrochloric acid (5M) at 0 0C with vigorous stirring. A solid precipitate was collected by filtration and washed with diethyl ether/hexanes (2:1) to yield a first batch of the title compound (43g). The filtrate was further extracted with ethyl acetate and the combined organic phases were dried over sodium sulphate and purified by column chromatography (10-80% ethyl acetate/hexanes) to yield another batch of the title compound (7g), in total gave 50 g (68%). 1H NMR (300 MHz, CDCI3): delta(ppm) 13-12 (br S, 1 H)1 8.08 (d, 1H), 6.52 (d, 1H), 4.3 (q, 2H), 4.21 (q, 2H)1 4.13 (s, 2H)1 1.29 (m, 6H).

Statistics shows that Propiolamide is playing an increasingly important role. we look forward to future research findings about 7341-96-0.

Reference:
Patent; NPS ALLELIX CORP.; WO2008/9125; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 6973-09-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6973-09-7 name is 5-Amino-2-methylbenzenesulfonamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a mixture of 5-amino-2-methylbenzenesulfonamide (20 gm) in ethanol (208 ml) and tetrahydrofuran (52 ml) was added 2,4-dichloropryrimidine (44 gm) and sodium bicarbonate (36 gm) at room temperature. The contents were heated to 70 to 75¡ã C. and maintained for 13 hours. The reaction mass was then cooled to 10¡ã C. and maintained for 2 hours. The reaction mass was filtered and the solvent was distilled off under vacuum at below 50 to 55¡ã C. to obtain a residual mass. To the residual mass was added ethyl acetate (100 ml) and stirred for 1 hour, filtered. The solid obtained was dried to give 15.5 gm of 5-(4-chloropyrimidin-2ylamino)-2-methylbenzenesulfonamide

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-2-methylbenzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; HETERO RESEARCH FOUNDATION; Reddy, Bandi Parthasaradhi; Reddy, Kura Rathnakar; Reddy, Dasari Muralidhara; Rao, Thungathurthy Srinivasa; Krishna, Bandi Vamsi; US2013/245262; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 122334-37-6, A common heterocyclic compound, 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide, molecular formula is C9H10ClNO2, 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.

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 6-bromo-4-(tert-butoxy)quinazoline (2.5 g, 8.89 mmol, 1.00 equiv) in tetrahydrofuran (100 mL). This was followed by the addition of n-BuLi (4.25 mL, 1.20 equiv) dropwise with stirring at -78 C. After 40 mins, to the mixture was added a solution of 4-chloro-N-methoxy-N-methylbenzamide (2.17 g, 10.87 mmol, 1.20 equiv) in tetrahydrofuran (20 mL). The resulting solution was stirred for another 30 min at 0 C. in a water/ice bath. The reaction was then quenched by the addition of water (10 mL), and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5), to yield of 4-(tert-butoxy)-6-[(4-chlorophenyl)carbonyl]quinazoline as a white solid.

The synthetic route of 122334-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Macielag, Mark Joseph; Zhang, Yue-Mei; DeCorte, Bart L.; Greco, Michael N.; (118 pag.)US2016/68512; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 129686-16-4, These common heterocyclic compound, 129686-16-4, name is 6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one, 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.

A. Synthesis of the intermediates Example A.1 a) Preparation of intermediate (1) A solution of 6-bromo-3,4-dihydro-lH-[l,8]naphthyridin-2-one (1.0 g, 4.4 mmol), tert- butyl acrylate (2.56 ml, 17.62 mmol) and N,N-diisopropylethylamine (1.46 ml, 8.81 mmol) in acetonitrile (20 ml) and DMF (7 ml) was stirred and degassed with nitrogen gas for 10 minutes. Tri-o-tolylphosphine (0.27 g, 0.88 mmol) and palladium (II) acetate (47% on Pd) (0.099 g, 0.44 mol) were added and the resulting mixture was microwaved (1600 W, 180C, 35 minutes). The reaction mixture was evaporated till dryness, taken up in a mixture of DCM/methanol (8/2) (50 ml), filtered through a short pad of celite and washed with DCM. The organic layer was washed with water, dried (MgS04), filtered and evaporated to dryness. The residue was taken up in cold ethanol (10 ml) and stirred at 5C for 5 minutes, the precipitate was filtered off, washed with cold ethanol (3 ml) and dried under vacuum to yield 950 mg intermediate (1).

The synthetic route of 129686-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; GUILLEMONT, Jerome, Emile, Georges; LANCOIS, David, Francis, Alain; MOTTE, Magali, Madeleine, Simone; KOUL, Anil; BALEMANS, Wendy, Mia, Albert; ARNOULT, Eric, Pierre, Alexandre; WO2013/21054; (2013); 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. 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 141449-85-6

A 50-mL round-bottom flask was charged with 2-fluoro-4-(trifluoromethyl)benzaldehyde (0.500 g, 2.60 mmol, 1.00 equiv) in dimethyl sulfoxide (10 mL), tert-butyl octahydropyrrolo[3,4-c]pyrrole-2-carboxylate (0.828 g, 3.90 mmol, 1.50 equiv), and potassium carbonate (1.08 g, 7.81 mmol, 3.00 equiv). The resulting solution was stirred overnight at 90 C. and quenched with water (20 mL). The mixture was extracted with ethyl acetate (3*20 mL) and the organic layers were combined, washed with brine (2*20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (1/3) to provide 0.580 g (58% yield) of tert-butyl 5-(2-formyl-5-(trifluoromethyl)phenyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate as a yellow solid. LCMS (ESI, m/z): 385 [M+H]+.

The synthetic route of 141449-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; WEBER, Olivia D.; (127 pag.)US2019/202801; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, 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. Safety of tert-Butyl (trans-4-hydroxycyclohexyl)carbamate

(1) To a solution of tert-butyl(trans-4-hydroxycyclohexyl)carbamate (1.08 g, 5.00 mmol) and 15-crown 5 (1.04 mL, 5.25 mmol) in tetrahydrofuran was added sodium hydride (60% dispersion in mineral oil, 440 mg, 11.0 mmol) at 0 C., followed by iodomethane (0.327 mL, 5.25 mmol) at 0 C. After being stirred for 2 hour, the reaction mixture was poured into water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, died over sodium sulfate, filtrated and concentrated in vacuo. The residue was purified by silica gel column chromatography to give tert-butyl(trans-4-methoxycyclohexyl)carbamate as a colorless solid (796 mg, 69%). MS (APCI): m/z 247 (M+NH4), 230 (M+H).

The synthetic route of 111300-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kawanishi, Eiji; Matsumura, Takehiko; US2011/160206; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 123986-64-1, 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. 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 281,1-Dimethylethyl [(4-{[3-{bis[(5-chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazol-1-yl]methyl}phenyl)methyl]carbamate; A solution of 5-chloro-N-[(5-chloro-2-thienyl)sulfonyl]-N-[4-(methyloxy)-1 H-indazol-3-yl]-2-thiophenesulfonamide (for a preparation see Intermediate 10)(400 mg, 0.763 mmol), triphenylphosphine (400 mg, 1.52 mmol) and 1,1-dimethylethyl{[4-(hydroxymethyl)phenyl]methyl}carbamate (Maybridge) (362 mg, 1.52 mmol) in THF (3 mL) was added at room temperature DIAD (0.300 mL, 1.52 mmol). The resulting mixture was stirred at 65 C. for 3 hours. The reaction mixture was partitioned between DCM (3 mL) and water (3 mL). The organic phase was separated, and the aqueous layer was further extracted with DCM (3 mL). The combined organic solutions were dried over an hydrophobic frit and evaporated under a nitrogen stream in a blowdown unit. The residue was loaded in dichloromethane on a silica (50 g) cartridge and purified by chromatography on Flashmaster II using a gradient of 0-100% dichloromethane-cyclohexane over 40 min. The appropriate fractions were combined and evaporated in vacuo to give the title compound (498 mg, 88%) as a gum.LCMS (System A) RT=1.48 min, ES+ve m/z 760/762 (M+NH4)+.

The synthetic route of tert-Butyl 4-(hydroxymethyl)benzylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hodgson, Simon Teanby; Lacroix, Yannick Maurice; Procopiou, Pauayiotis Alexandron; US2010/216860; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 880166-10-9,Some common heterocyclic compound, 880166-10-9, name is Methyl 1-((tert-butoxycarbonyl)amino)cyclobutanecarboxylate, molecular formula is C11H19NO4, 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.

To a stirred suspension of LiAlH4(1.8 g, 46.4 mmol) in dry THF (15 ml), was slowly added a solution of methyl l-((tert-butoxycarbonyl)amino)cyclobutane-l-carboxylate (step 1, 5.32g, 23.2 mmol) in THF (15 ml) at 0 C. The reaction mixture was brought to room temperature and stirred for about 3 hours. After completion of the reaction (monitored by TLC), the reaction mixture was quenched by the sequential addition of 1.8 mL of H20, 5.4 mL of 15% aq. NaOH and 5.4 mL of H20. The mixture was then poured into EtOAc (100 ml) and stirred for about 30 minutes. The reaction mixture was filtered through celite, dried over Na2S04and concentrated under reduced pressure. The product was isolated by flash column chromatography on silica gel using (EtOAc: hexane-70:30) to give the desired product (3.7 g, yield: 80%) as an oil. 1H NMR (300 MHz, DMSO-d6): delta 6.62 (s, 1H), 4.67 (t, J = 5.4 Hz, 1H), 3.41 (d, J = 5.4 Hz, 2H), 2.22-2.09 (m, 2H), 2.01-1.90 (m, 2H), 1.65-1.57 (m, 2H), 1.36 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-((tert-butoxycarbonyl)amino)cyclobutanecarboxylate, its application will become more common.

Reference:
Patent; HETERO RESEARCH FOUNDATION; BANDI, Parthasaradhi Reddy; KURA, Rathnakar Reddy; ADULLA, Panduranga Reddy; GAZULA LEVI, David Krupadanam; MUKKERA, Venkati; NEELA, Sudhakar; LANKA, Vl Subrahmanyam; (170 pag.)WO2017/17630; (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. 389890-43-1, name is tert-Butyl (cis-3-hydroxycyclobutyl)carbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl (cis-3-hydroxycyclobutyl)carbamate

MsCl (5.386 g, 46.83 mmol, 2.00 eq.) was added dropwise to a cold solution of tert-butyl N-[trans-3- hydroxycyclobutyl] carbamate (4.379 g, 23.39 mmol, 1.00 eq.) and TEA (7.095 g, 70.12 mmol, 3.00 eq.) in dichloromethane (25 mL at 0C. The resulting solution was stirred for 3 hours at room temperature and it was then diluted with 200 mL of dichloromethane. The resulting mixture was washed with water (2×100 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was recrystallized from dichloromethane/hexane in the ratio of 1 : 1 to give 5.548 g (89%) of tert-butyl N-[cis-3- (methanesulfonyloxy)cyclobutyl] carbamate as an off-white solid.

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; PROTEOSTASIS THERAPEUTICS, INC.; LEE, Po-shun; (180 pag.)WO2017/40606; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics