Amides-buliding-blocks

Reference of 6971-74-0, These common heterocyclic compound, 6971-74-0, name is N-Tosylbenzamide, 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: N-Benzoylsulfonamide 1a (27.5 mg, 0.1 mmol), [RhCl2Cp*]2 (1.2 mg, 0.002 mmol), and Cu(OAc)2¡¤H2O (40.0 mg, 0.20 mmol) were loaded in a dry vial, which was subjected to evacuation/flushing with dry argon three times. An anhydrous toluene (1.0 mL) solution of ethyl diazoacetate 4a (30 muL, 0.30 mmol) was syringed into the mixture, which was then stirred at 130 C for 24 h or until the starting material had been consumed as determined by TLC. Upon cooling to room temperature, all volatiles were evaporated and the residue was purified by preparative TLC (ethyl acetate/hexane=1:2) to give isoindolinone 3i in 80% yield.

The synthetic route of 6971-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhu, Chen; Falck, John R.; Tetrahedron; vol. 68; 45; (2012); p. 9192 – 9199;,
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 3984-14-3 as follows. HPLC of Formula: C2H8N2O2S

2-(1H-indoi-6-yl)-3-[4-(tetrahvdro-pyran-4-yioxymethyi)-phenyiethynvi-benzoic acid (45.1 rng, 0.1 mrnol) and dimethylsulfarnoyl amine (149 mg, 0.14 rnrnoi) were dissolved in N,Ndimethyiforinarnide (1 mL), followed by the addition of 1-ethyl-3-(3-dimethyiaminopropyl)carbodiimide hydrochloride (1.2 eq), 4-dimethylarninopyii dine (2 eq) and hydroxybenzotriazole (1.2 eq). The reaction was stirred at room temperature for 16 hours. The solvent was then evaporated to dryness and reaction mixture was purified by preparative HPLC to give product as an off-white solid in 68% yield. ?H NMR (300 MHz, CDCI3) d ppm 8.39 (hr. s., I H) 7.71-7.86 (in, 3 Fl) 7.54 (s, I H) 7.39-7.51 (m, 2 H) 7.20-733 (m, 4 H) 716 (d, .J=7.92 Hz, 2 H) 7.01 (d, J=8.21 Hz, 2 H) 6.63 (br. s.,1 H) 4.49 (s, 2 H) 3.88-4.06 (m, 2 H) 3.37-3.61 (in, 3 H) 2.56 (s, 6 H) 1.82-1.99 (m, 2 H) 1.54-1.75 (in. 2 H,). MS m/z (M-i-H) 558.2.

According to the analysis of related databases, 3984-14-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE WISTAR INSTITUTE OF ANATOMY AND BIOLOGY; MESSICK, Troy E.; SMITH, Garry R.; REITZ, Allen B.; LIEBERMAN, Paul M.; MCDONNELL, Mark E.; ZHANG, Yan; CARLSEN, Marianne; CHEN, Shuai; (205 pag.)WO2016/183534; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 389890-42-0, 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. 389890-42-0, name is tert-Butyl (trans-3-hydroxycyclobutyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 26-b To a solution of intermediate 8-b (2.0 g, 10.7 mmol) in anhydrous THF (53 ml) cooled to 0C was slowly added a 1.0 M solution of LiAIH4 in THF (32.0 ml, 31.0 mmol). After the addition was completed, the reaction was warmed to room temperature, stirred at 65C for 2 hours and then cooled to 0C. 15% aqueous NaOH was then added and after stirring for 15 minutes the reaction was filtered. The filtrate was concentrated under reduced pressure. Purification by silica gel chromatography provided intermediate 26-b as a white solid.

The synthetic route of tert-Butyl (trans-3-hydroxycyclobutyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMASCIENCE INC.; LAURENT, Alain; ROSE, Yannick; MORRIS, Stephen J.; (184 pag.)WO2016/187723; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 150349-36-3,Some common heterocyclic compound, 150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, molecular formula is C9H20N2O2, 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.

l,2-Dichloro-3-nitro-benzene (1.0 g, 5.2 mmol), (3-Amino-propyl)-methyl-carbamic acid tert- butyl ester (2.25 g, 11.9 mmol) and diisopropylethylamine (1.8 mL, 10.4 mmol) were combined and heated to about 100 0C. After about 3 days the reaction mixture was diluted with diethyl ether (200 mL) and IN HCl (200 mL). The organic layer was separated, washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to provide 1.8 g of [3-(2-Chloro-6-nitro- pheny]amino)-propyl]-methyl-carbamic acid tert-butyl ester as an oil which was used in subsequent reactions without further purification. RP-HPLC R1 7.51 min. (table 1, method a); m/z: (M + H)+ 244.0. Preparation #9 [3-(2-chloro-6-nitro-phenylamino)-propyl]-methyl-carbamic acid tert-butyl ester l,2-Dichloro-3-nitro-benzene (1.0 g, 5.2 mmol), (3 -Amino-propyl )-methyl-carbamic ac id tert-butyl ester (2.25 g, 11.9 mmol) and diisopropylethylami?e (1.8 mL, 10.4 mmol) were combined and heated to about 100 0C. After about 3 days the reaction mixture was diluted with diethyl ether (200 mL) and IN HCl (200 mL). The organic layer was separated, washed with brine, dried (JSIa2SO4), filtered and concentrated in vacuo to provide 1.8 g of [3-(2-Chloro-6-nitro- phenylamino)-propyl]-methyl-carbamic acid tert-butyl ester as an oil which was used in subsequent reactions without further purification. RP-HPLC R1 7.51 min. (table 1, method a); m/z: (M + H)+ 244.0- To a solution of the above nitro aniline in acetic acid (53 mL) at room temperature was added iron powder (1.2 g, 21.2 mmol). After stirring for about 15 hours the reaction mixture was filtered and concentrated in vacuo. The crude product was dissolved in diethyl ether and washed with a solution of 2N NaOH that had been saturated with EDTA. The organic layer was further washed with brine, dried with Na2SO4, filtered and concentrated in vacuo to provide [3-(2-Amino-6-chloro-rhohenylamino)-propyl]-methyl-carbamic acid tert-butyl ester as a brown oil that was used in subsequent reactions without further purification. RP-HPLC R, 6.05 min. (table 1, method a). To a solution of the crude phenylene diamine in EtOH (98 mL) was added NaOAc (1.8 g, 22 mmol) followed by a 5 N solution of cyanogen bromide in acetonile (1.4 mL, 7.2 mmol). After stirring for about 20 hours at room temperature the reaction mixture was concentrated in vacuo. The crude reaction mixture was diluted with Et2O (200 mL) and 2 N NaOH (200 mL). The organic layer was separated, washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography on silica gel (gradient elution 5-10% MeOH/CH2Cl2, containing 1% Et3N) to provide 1.3 g of [3-(7-Chloro-2- imino-2,3-dihydro-ben2oimJdazol-l-yl)-propyl]-methyl-carbamic acid tert-butyl ester as a brown oil. RP-HPLC R, 6.05 min (table 1, method a), m/z: (M+H)+ 339.0, 341.1 (3:1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(N-Boc-N-methylamino)propylamine, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2007/84728; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6973-09-7, name is 5-Amino-2-methylbenzenesulfonamide, 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. Application In Synthesis of 5-Amino-2-methylbenzenesulfonamide

To a stirred suspension of the product of Intermediate Example 4 (1 .1 g, 3.7 mmol) in 10 mL of THF, was added 5-amino-2-methylbenzenesulfonamide (0.70 g, 3.8 mmol, 1 .0 equiv) at room temperature. The reaction mixture was heated at reflux for 3 h, then 4 M HCI in 1 ,4-dioxane (18 muL, 0.072 mmol) was added in one portion. After 5 h, the suspension was cooled to room temperature, and filtered. The resulting solid was washed with 16 mL of THF and dried in the air to yield 1 .6 g (92%) of 5-({4-[(2,3- dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl}amino)-2-methylbenzene sulfonamide monohydrochloride as a light yellow solid.

The synthetic route of 6973-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/20564; (2006); 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. 131818-17-2, name is tert-Butyl (4-bromophenyl)carbamate, A new synthetic method of this compound is introduced below., Product Details of 131818-17-2

b) tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate A mixture of tert-butyl N-[(4-bromophenyl)carbamate (5.95 g, 0.0219 mol), diboron pinacol ester (6.67 g, 0.0263 mol), [1.1′-bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (1:1) (0.536 g, 0.00066 mol) and potassium acetate (6.47 g, 0.066 mol) in N,N-dimethylformamide (120 mL) was heated at 80 C. under an atmosphere of nitrogen for 16 hours. The mixture was allowed to cool to ambient temperature and the solvent removed under reduced pressure. Dichloromethane (100 mL) was added to the residue and the resulting solid was removed by filtration through a pad of Celite. The filtrate was concentrated to leave a yellow oil which was purified by flash chromatography on silica using ethyl acetate/n-heptane (7:93) as mobile phase. The resulting fractions were concentrated, the residue was triturated in n-heptane and the precipitate collected by filtration to yield tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (6.0 g, 0.0188 mol) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta 9.50(s, 1H), 7.55 (d, 2H), 7.46 (d, 2H), 1.47 (s, 9H), 1.27 (s, 12H).

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; Abbott Laboratories; US6921763; (2005); B2;,
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

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

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

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