Category: amides-buliding-blocks

Electric Literature of 1888-91-1, A common heterocyclic compound, 1888-91-1, name is N-Acetylcaprolactam, molecular formula is C8H13NO2, 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.

General procedure: Under an argon atmosphere, liquid NH3 (25 mL) was condensedin a two-neck round-bottom flask immersed in a dry ice coolingbath and equipped with a dry ice reflux condenser. Aldehyde(7.34 mmol) was added, and the resulting solution (or suspension)was stirred for 1 h. KMnO4 (7.34 mmol, 1.16 g) was added,the cooling bath was removed, and the reaction mixture wasstirred for another hour with gentle reflux of NH3. Na2SO3 (22.0mmol, 2.78 g) was added, the reflux condenser was removed,and the NH3 was allowed to evaporate spontaneously. The darkbrownresidue was treated with 6 M HCl (30 mL), and theresulting precipitate was filtered, washed with H2O (100 mL)and sat. aq NaHCO3 (20 mL). All products were recrystallizedfrom EtOH.

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; Antoniak, Damian; Sakowicz, Arkadiusz; Loska, Rafal; Makosza, Mieczyslaw; Synlett; vol. 25; 9; (2014);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 201162-53-0, These common heterocyclic compound, 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, 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 solution of tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate (1 g, 4.71 mmol, 1.00 equiv), potassium carbonate (1.3 g, 9.41 mmol, 2.00 equiv), 5-chloropyridin-2-carbonitrile (651 mg, 4.67 mmol, 1.00 equiv) in DMF (10 mL) was stirred for 2 h at 80 C. in an oil bath. The solids were filtered out. The resulting solution was extracted with 3*20 mL of ether and the organic layers combined. After concentration, the residue was applied onto a silica gel column eluting with EtOAc/petroleum ether (1:2) to afford 1 g (68%) of the title compound as a solid. LCMS (ESI, m/z): 315.17 [M+H]+

Statistics shows that 3-Boc-3,8-Diazabicyclo[3.2.1]octane is playing an increasingly important role. we look forward to future research findings about 201162-53-0.

Reference:
Patent; Ribon Therapeutics Inc.; Vasbinder, Melissa Marie; Schenkel, Laurie B.; Swinger, Kerren Kalai; Kuntz, Kevin Wayne; (410 pag.)US2019/330194; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 103361-99-5, name is 7-Fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, molecular formula is C8H6FNO2, 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. Formula: C8H6FNO2

To a stirred solution of step 2 intermediate (2.7 g, 16.157 mmol) in sulphuric acid (3 ml) a mixture of nitric acid (69 %, 0.72 ml, 16.157 mmol) and concentrated sulphuric acid (2 ml) was drop wise added at 0 C under nitrogen atmosphere. The reaction mixture was stirred at 0 C for 30 min. The reaction mixture was quenched with ice-cooled water and solid was precipitated. The precipitated solid was dissolved in ethyl acetate (30 ml) and washed with aqueous saturated solution of sodium bicarbonate (150 ml). The ethyl acetate layer was dried and filtered and dried (Na2S04) and concentrated to yield 2.6 g of product as yellow solid. 1H NMR (300 MHz, DMSO-d6) delta 4.79 (s, 2H), 7.26 (d, J = 12.0 Hz, 1H), 7.63 (d, / = 7.2 Hz, 1H), 1 1.03 (br s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103361-99-5, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; CHAUDHARI, Sachin Sundarlal; KUMAR, Sukeerthi; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; WO2013/153539; (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. 75175-77-8, name is 3-(4-Fluorophenyl)-N,N-dimethylacrylamide, A new synthetic method of this compound is introduced below., SDS of cas: 75175-77-8

General procedure: With a mixture of N,N-Dimethylenaminones 1 (1.0 mmol), isatins 2 (0.5 mmol), ammonium acetate 3 (1.0 mmol) in AcOH (1 mL) and EtOH-water (1:4) (5 mL), the reaction mixture was stirred at 80 C for 6 h until TLC indicated that the reaction was completed. The reaction mixture was allowed to cool to room temperature, neutralised with a saturated solution of Na2CO3 to pH 8-9, and then was extracted with ethyl acetate (2 ¡Á 30 mL). The organic phase was washed with water (20 mL) and the organic layer dried over Na2SO4, and concentrated under reduced pressure. The crude product was chromatographed onsilica gel (200-300 mesh) using a mixture of petroleum ether and ethyl acetate as eluent to afford the product 4.

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; Zhou, Pan; Hu, Biao; Lu, Lingling; Huang, Rong; Yu, Fuchao; Journal of Chemical Research; vol. 41; 9; (2017); p. 513 – 516;,
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. 6269-91-6, name is 2-Methyl-5-nitrobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H8N2O4S

To a solution of 3-aminosulfonyl-4-methylnitrobenzene in dichloromethane and methanol was added 10percent Pd/C and the mixture shaken under a hydrogen atmosphere at 50 psi for 15 minutes.The mixture was filtered through diatomaceous earth and the filter cake was washed with methanol.The combined organic solvents were concentrated under reduced pressure to give crude product, which was further purified by flash column chromatography (ethyl acetate:hexanes 1:1) to give 3-aminosulfonyl-4-methylaniline, LCMS: purity: 87percent; MS (m/e): 187 (MH+).

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 6269-91-6.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; US2012/232106; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 6292-59-7, 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 6292-59-7 as follows.

Step-4:Preparation of 4-(14-dimethylethyl)-N-[6-chloro-5-(2-methoxyphenoxy)[2,2′-bipyrimidin]-4- yl|benzenesulfonamide (VII).5-(2-Methoxyphenoxy)-2-(pyrimidin-2-yl)-tetrahydropyrimidin-4,6-dione (IV) (10Og,320.22mmol) was added to phosphorous oxychloride (196.4g). The resulting reaction mass was slowly heated to 103-1050C and stirred for 4 hrs. The reaction mass was added to a mixture of toluene (450ml) and water (350ml) at 20-500C and treated with 30percent w/w aqueous sodium hydroxide solution (271.5ml) at 70-800C. The organic layer was separated and treated with activated carbon (7g) at 80-900C for 30min, filtered through hyflo and washed with hot toluene (300ml). 4-(l ,l-Dimethylethyl)benzene sulfonamide (VI) (68.3g, 320.2mmol) was added to the filtrate, followed by potassium carbonate (53.03g, 384.27 mmol) and tetrabutylammonium bromide (3.19g, 9.59 mmol) were added, heated to reflux temperature and separated water azeotropically for 2 hrs, the reaction mass was cooled to 20-250C, filtered the solid and dried. Further, the solid was added to DM water and acidified to pH 0.5 to 0.7 with hydrochloric acid. The solid was filtered washed with DM water and dried to yield 144.5g of title product.Chromatographic purity: 97.92percent (by HPLC, by area normalization)

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; AUROBINDO PHARMA LIMITED; BRAJESH, Kumar, Sinha; KONDURU, Rajasekhara, Raju; BUDIDET, Shankar, Reddy; VADDI, Pandu, RangaRao; AMINUL, Islam; MEENAKSHISUNDERAM, Sivakumaran; WO2011/24056; (2011); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 1943-79-9,Some common heterocyclic compound, 1943-79-9, name is Phenyl methylcarbamate, molecular formula is C8H9NO2, 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 solution of (2R,4S,4aS)-8-amino-2,4-dimethyl-l,2,4,4a-tetrahydro-2’H,6H-spiro[l,4- oxazino[4,3-a]quinoline-5,5′-pyrimidine]-2′,4′,6′(leta,3eta)-trione (Intermediate 34, 250 mg, 0.74 mmol) in anhydrous THF (20 mL) at 0 0C was added triethylamine (2.5 g, 0.024 mol) followed by methylphenoxycarbamate (0.66 mmol) and the mixture was refluxed for 48 hours. Methyl phenoxy carbamate was prepared by stirring methyl amine (1 eq.) and phenylchloro formate (1 eq.) in DCM at -30 0C to room temperature for 4 hours, and was purified by column chromatography. The reaction mixture was quenched with HCl (IN, 30 ml) and extracted with ethyl acetate (5 x 20 mL). The organic phase was dried over anhydrous sodium sulphate and was concentrated under reduced pressure. The residue thus obtained was washed with ether and further purified by preparative TLC to give the title compound. Yield: 20 mg (70%). MS(ES) MH+: 402.2 for Ci9H23N5O5 1H NMR (400 MHz, DMSO-d6) delta : 0.9 (d, 3H), 1.1 (d, 3H), 2.5 (d, 3H), 2.9 (d, IH), 3.1 (d, IH), 3.5 (d, IH), 3.55 (m, 2H), 3.85 (d, IH), 5.8 (m, IH), 6.7 (d, IH), 6.9 (s, IH), 7.1 (d, IH), 11.7 (bs, 2H).

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/4382; (2009); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 144912-84-5, 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. 144912-84-5 name is tert-Butyl (3-amino-2-hydroxypropyl)carbamate, 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.

The obtained crude product of ((S)-3-amino-2-hydroxypropyl)carbamic acid tert-butyl ester (283 mg, 1.487 mmol) and 5-[2-amino-6-(3-carboxylpropylsulfanyl)pyrimidin-4-yl]-2,4-dimethylbenzoic acid tert-butyl ester (300 mg, 0.744 mmol) obtained in Step 1 of Example 2-1 were dissolved in N,N-dimethylformamide (7 ml), and then 1-hydroxybenzotriazole monohydrate (377 mg, 2.462 mmol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (152 mg, 2.2 mmol) were sequentially added thereto. The resulting mixture was stirred at room temperature for three hours. The reaction solution was diluted with ethyl acetate, and then washed with a saturated aqueous ammonium chloride solution (twice) and a saturated aqueous sodium bicarbonate solution (twice). After the organic layer was dried over anhydrous sodium sulfate, the inorganic salt was removed by filtration. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: dichloromethane:methanol = 20:1) to yield ((S)-3-amino-2-hydroxypropyl)carbamic acid tert-butyl ester. The obtained ((S)-3-amino-2-hydroxypropyl)carbamic acid tert-butyl ester was dissolved in dichloromethane (20 ml), and then water (0.1 ml) and trifluoroacetic acid (10 ml) were added thereto. After the solution was stirred at room temperature for one hour, the solvent was distilled off under reduced pressure to yield a crude product of 5-{2-amino-6-[2-((R)-3-amino-2-hydroxypropylcarbamoyl)ethylsulfanyl]pyrimidin-4-yl}-2,4-di methylbenzoic acid di(trifluoroacetate).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (3-amino-2-hydroxypropyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; EP2119718; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 152192-95-5, name is tert-Butyl ethyl(2-hydroxyethyl)carbamate, 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 152192-95-5, COA of Formula: C9H19NO3

To a mixture of tert-butyl ethyl(2-hydroxyethyl)carbamate (1.89 g) obtained in Reference Example 19 and ethyl acetate (20 mL) were added acetic anhydride (1.04 mL), pyridine (0.89 mL) and 4-dimethylaminopyridine (0.061 g). After stirring at room temperature for 3 hrs., ethyl acetate (50 mL) was added, and the mixture was washed with water (50 mL), a 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL). After drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. A 4N hydrogen chloride – ethyl acetate solution (10 mL) was added to the residue, and the mixture was stirred at room temperature for 1 hr. Ethyl acetate (10 mL) and diethyl ether (20 mL) were added, and the precipitated solid was collected by filtration. The solid was dried under reduced pressure to give the title compound (1.54 g) as a white solid.1H-NMR(DMSO-d6) : 1.22 (3H,t,J=7.3Hz), 2.07 (3H,s), 2.95(2H,q,J=7.3Hz), 3.15(2H,t,J=5.3Hz), 4.24-4.30(2H,m), 9.17 (2H,br).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl ethyl(2-hydroxyethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1607088; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 23530-40-7, A common heterocyclic compound, 23530-40-7, name is N-Methyl-2-nitrobenzenesulfonamide, molecular formula is C7H8N2O4S, 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.

2-Trityl-2H-tetrazol-5-ylmethanol (2.00 g, 5.84 mmol), N-methyl-2-nitrobenzenesulfonamide (1.64 g, 7.59 mmol) and triphenylphosphine (1.53 g, 5.84 mmol) were dissolved in a mixed solvent of tetrahydrofuran (30 mL) and toluene (20 mL), then a solution of diethyl azodicarboxylate in toluene (40%, 2.65 mL, 5.84 mmol) was added thereto and the mixture was stirred at room temperature for throughout a night. After the mixture was passed through a silica gel column (eluting solvent: ethyl acetate/hexane = 40/60) to remove original point components, acetone (5 mL) and acetonitrile (25 mL) were added to the residue prepared by concentrating in vacuo. Mercaptoacetic acid (0.73 mL, 11 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (3.1 mL, 21 mmol) were added to the resulting suspension and the mixture was stirred at 60C for 7 hours. The reaction solution was concentrated and the residue was dissolved in ethyl acetate. The resulting solution was washed with a saturated aqueous solution of sodium bicarbonate and a saturated saline solution successively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by a silica gel chromatography (eluting solvent: triethylamine/ethyl acetate = 1/99) to prepare N-methyl-N-(2-trityl-2H-tetrazol-5-yl)methylamine (396 mg, 1.11 mmol, yield: 19.0%). 1H NMR (CDCl3) delta(ppm): 2.45 (s, 3H), 4.07 (s, 2H), 7.07-7.36 (m, 15H).

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; KYOWA HAKKO KOGYO CO., LTD.; EP1547616; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics