Category: amides-buliding-blocks

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

Ethyl magnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a few minutes to a clear colorless solution of 5-bromo-1-methyl-1H-imidazole (10.4 g, 64.4 mmol) in THF (100 mL) under a nitrogen atmosphere in an ice bath. A white precipitate formed during the addition. The mixture was removed from the ice bath and was stirred for 20 minutes, then was again cooled in an ice bath before addition of 4-chloro-N-methoxy-N-methylbenzamide (10.7 g, 53.6 mmol, Intermediate 43: step a). The resulting white suspension was stirred overnight at room temperature. The reaction was quenched by addition of saturated aqueous NH4Cl and diluted with water. The mixture was partially concentrated to remove THF and was diluted with DCM. The mixture was acidified to pH 1 with 1 N aqueous HCl, then neutralized with saturated aqueous NaHCO3. The phases were separated and the aqueous phase was further extracted with DCM. The organic extracts were washed with water, then were dried (Na2SO4), filtered, and concentrated, affording a white solid. The crude product was triturated with a mixture of EtOAc:heptanes (1:1, 150 mL). The precipitated solid was collected by vacuum filtration, washing with heptanes, to afford the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-N-methoxy-N-methylbenzamide, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
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Synthetic Route of 33545-97-0, A common heterocyclic compound, 33545-97-0, name is N,N’-Di-Boc-1,4-butanediamine, molecular formula is C14H28N2O4, 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.

Commercially available putrescine 1 is (bis)-N-Boc protected to produce compound 2 (85.2% yield). Compound 2 is used to alkylate qty. 2 equivalents of propargyl bromide in the presence of sodium hydride producing compound 3 (59.5% yield). Yields in that transformation are further enhanced by using a mixture of dimethylformamide (“DMF”) and tetrahydrofuran (“THF”) in a ratio of 1:5. The propargyl groups in compound 3 are converted to the corresponding allenes in the presence of CuBr, formaldehyde, and diisopropylamine to yield intermediate compound 4 (38.7% yield). Compound 4 is de-protected in the presence of HCl to yield the desired target molecule MDL 72,527 (white solid, 65.8% yield). [00097] HPLC method of quantitation of MDL, natural polyamines and their acetyl derivatives in cell extracts as well as in human and animal serum is standardized. Therefore, the pharmacokinetics and pharmocodynamics of MDL 72,527 may be determined.

The synthetic route of 33545-97-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; WO2007/130589; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35303-76-5, name is 4-(2-Aminoethyl)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 35303-76-5, HPLC of Formula: C8H12N2O2S

General procedure: Starting dichlorotriazinyl benzenesulfonamide (1 mmol; 0.320 g of4- [(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzene-1-sulfonamide, 0.334 g of4-{[(4,6-dichloro-1,3,5-triazin-2-yl)amino]methyl}benzene-1-sulfonamide or 0.348 g of4-{2-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-ethyl}benzene-1-sulfonamide)) was dissolved in20 mL of DMF. Then 1 mmol (0.138 g) of solid anhydrous potassium carbonate was added in smallportions and the mixture was stirred for 10 min. Then 1 mmol of the appropriate nucleophile wasadded portion wise. Finally, 2.5% mol. of supported Cu(I) ions (312 mg of catalyst) was addedinto the reaction mixture. Reaction was stirred at 35 C until the maximum conversion of startingmaterial is achieved (monitored by TLC). After completion of the first reaction step, 1 mmol of thesecond nucleophile and 1 mmol (0.138 g) of anhydrous potassium carbonate were added into thereaction mixture. The reaction mixture was then stirred at 100 C until the maximum conversion of anucleophile was determined (monitored by TLC). After completion of a reaction, the catalyst andsalt were filtered o. Crushed ice was then added into the solution and the formed precipitate wascollected by filtration. The crude product was dissolved in acetone and precipitated by the addition ofisopropyl alcohol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(2-Aminoethyl)benzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Article; Havrankova, Eva; Csoellei, Jozef; Pazdera, Pavel; Molecules; vol. 24; 19; (2019);,
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., Quality Control of tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Example 257B 5-(1-Phenyl-1H-pyrazol-4-yl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic Acid tert-butyl Ester To the product of Example 6C (0.5 g, 2.4 mmol) in 15 mL toluene in a pressure tube was added the product of Example 257A (0.68 g, 3.06 mmol), tris(dibenzylideneacetone)dipalladium (0) (Pd2(dba)3, Strem, 43 mg, 0.047 mmol), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, Strem, 59 mg, 0.094 mmol), and tert-BuONa (0.362 g, 3.8 mmol). This mixture was warmed to 85 C. and stirred for 18 h. At this point, the reaction was incomplete, so additional Pd2(dba)3 (43 mg, 0.047 mmol) and BINAP (59 mg, 0.094 mmol) were added and the mixture stirred for an additional 24 h. The reaction was cooled to ambient temperature, filtered through Celite diatomaceous earth, concentrated under reduced pressure and purified via flash column chromatography (SiO2, 50% hexanes-EtOAc) to give the title compound (40 mg, 0.113 mmol, 5% yield). MS (DCl/NH3) m/z 355 (M+H)+.

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; Basha, Anwer; Bunnelle, William H.; Dart, Michael J.; Gallagher, Megan E.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Ryther, Keith B.; Tietje, Karin R.; Mortell, Kathleen H.; Nersesian, Diana L.; Schrimpf, Michael R.; US2005/101602; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, 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 201162-53-0, Recommanded Product: 201162-53-0

Tertbutyl 3,8-diazabicyclo[3 .2.ljoctane-3-carboxylate (250 mg, 1.18 mmol), 5-bromopicolinic acid (0.309g, 1.53 mmol), sodium 2-methylpropan-2-olate (0.283 g, 2.94 mmol), methanesulfonato(2-dicyclohexylphosphino-2?,6?-di-i-propoxy- 1,1 ?-biphenyl)(2-amino- 1,1biphenyl-2-yl)palladium(II) (0.04 9 g, 0.05 9 mmol) and 1 ,4-dioxane (4 mL) were charged in a vial. The headspace was flushed with nitrogen and the reaction mixture was degassed using 4 cycles of vacuum and nitrogen refilling. The reaction was heated at 110 C for 36 h then cooled to room temperature. Silica gel was added and the solvent was removed under vacuum. The desired product was purified by silica gel chromatography (eluting with hexane/ ethyl acetatemethanol). LCMS M/Z (M+H) 334.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Boc-3,8-Diazabicyclo[3.2.1]octane, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; COTE, Alexandre; CRAWFORD, Terry; DUPLESSIS, Martin; GOOD, Andrew, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F. Anthony; TANG, Yong; TAYLOR, Alexander, M.; (271 pag.)WO2016/138114; (2016); A1;,
Amide – Wikipedia,
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Reference of 112257-19-9, 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. 112257-19-9, name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 3-(4-isopropoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehyde (3.0 g, 9.54 mmol, 1.00 equiv) and tert-butyl N-methyl-N-[2-(methylamino)ethyl]carbamate (2.2 g, 11.69 mmol, 1.22 equiv) in 1,2-dichloroethane (30 mL) at room temperature was added NaBH(OAc)3 (4.1 g, 19.34 mmol, 2.03 equiv) in portions. The resulting solution was stirred at room temperature overnight and then diluted with 300 mL of dichloromethane. The resulting mixture was washed with 3*100 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 1-3percent MeOH in CH2Cl2 to give 4.0 g (86percent) of tert-butyl 2-(((3-(4-isopropoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate as a yellow oil. LCMS (method D, ESI): RT=1.76 min, m/z=487.0 [M+H]+.

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, tert-Butyl methyl(2-(methylamino)ethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, RICHARD; MITCHELL, LORNA HELEN; SHAPIRO, GIDEON; BORIACK-SJODIN, PAULA ANN; MORADEI, OSCAR MIGUEL; JIN, LEI; DUNCAN, KENNETH W.; US2014/323537; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 227940-71-8, name is tert-Butyl 7-benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate, 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 227940-71-8, Safety of tert-Butyl 7-benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

Trifluoro acetic acid (TFA) (2.25ml, 5eq, 0.03 mol) was injected to the stirring suspension of compound 12 (2.0g, l eq, 0.006mol) in DCM at 0C and allowed to stir at 25C (25-35C). Then reaction mixture was made alkaline by adding 20% aq. solution of Na2C03 and resulting mixture was extracted with dichloromethane (3 chi 50ml) and organics were washed with brine. The combined organics were dried with anhydrous Sodium sulphate and concentrated to obtain yellow oily liquid ( 1.641 g). Yield: 90% ; IR(Neat): 3451.4, 2924.6, 1610.0, 1450.4 cm” ;1H NMR (300MHz, CDC13, ppm): 87.37-7.27 (m, 5H, Ph-H); 3.49-3.41 (m, 4H, ChbPh, 2xNCH); 3.31-3.27 (d, J=12Hz, 2H, 2*NCH); 3.19-3.1 1 (m, 2H, 2> NCH); 2.49-2.45 (d, J=12Hz, 2H, 2xNCH); 2.12-2.07 (m, 2H, 2*CH); 1.93- 1.89 (d, J= 12Hz, I H, bridge CH); 1.79- 1.75 (d, J=12Hz, IH, bridge CH); MS (ESI):m/z = 217 (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; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; DIKSHIT, Dinesh Kumar; KARUNAKARAN SASIKALA, Anil Kumar; DIKSHIT, Madhu; BARTHWAL, Manoj Kumar; MISRA, Ankita; JAIN, Manish; WO2015/44951; (2015); A1;,
Amide – Wikipedia,
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Synthetic Route of 67279-23-6, 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. 67279-23-6, name is 2,3,5,6,7,8-Hexahydrophthalazine-1,4-dione, This compound has unique chemical properties. The synthetic route is as follows.

Step 2: Preparation of 1,4-dichloro-5,6,7,8-tetrahydrophthalazine (compound 1c) The compound 1b (1 g, 6.02 mmol) was dissolved into phosphorus oxychloride (8 ml). The air in the system was replaced 3 times with nitrogen gas. The system was warmed up to a temperature of 110 C. and stirred for 3 h. The reaction was stopped and then naturally cooled. The reaction solution was slowly dripped into ice water. The mixture was adjusted to pH 10 with a 1N sodium hydroxide aqueous solution and extracted 3 times with ethyl acetate. Organic phases were combined, and the organic phase was washed with saturated brine and concentrated to dry, to obtain a compound 1c (1.1 g).

The chemical industry reduces the impact on the environment during synthesis 2,3,5,6,7,8-Hexahydrophthalazine-1,4-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Terns, Inc.; YU, Shanghai; LI, Ben; (28 pag.)US2020/190064; (2020); A1;,
Amide – Wikipedia,
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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. 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H8ClNO

7-(5-Methoxy-l//^-indol-3-yl)-l-methyl-6 osyl-l,6-dihydropyrazolo[3,4-J]pyrrolo[2,3-ft]pyridine (0.100 g, 0.212 mmol; Preparation No.P.1.1) and 60 wt% NaH (0.009 g, 0.212 mmol) were suspended in DMF (3 mL). After about 10 min, 2-chloro-A^,A^-dimethylacetamide (0.052 g, 0.424 mmol, Pfaltz-Bauer) was added and mixture was stirred at rt. After about 1 h additional 60 wt% NaH (0.005 g, 0.212 mmol) was added and the mixture was heated to about 40 C for about 16 h. The mixture was concentrated in vacuo and purified on a 4 g silica column eluting with EtOAc to provide 2-(5-methoxy-3-(l-methyl-6-tosyl-l,6-dihydropyrazolo[3,4-dJpyrrolo[2,3-bJpyridin-7- yl)-lH-indol-l-yl)-N,N-dimethylacetamide (0.097 g, 82%): LC/MS (Table 2, Method c) Rt = 1.46 min; MS m/z 557 (M+H)+.

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 2675-89-0.

Reference:
Patent; ABBOTT LABORATORIES; WISHART, Neil; ARGIRIADI, Maria A.; BREINLINGER, Eric C.; CALDERWOOD, David J.; ERICSSON, Anna M.; FIAMENGO, Bryan A.; FRANK, Kristine E.; FRIEDMAN, Michael; GEORGE, Dawn M.; GOEDKEN, Eric R.; JOSEPHSOHN, Nathan S.; LI, Biqin C.; MORYTKO, Michael J.; MULLEN, Kelly D.; SOMAL, Gagandeep; STEWART, Kent D.; VOSS, Jeffrey W.; WALLACE, Grier A.; WANG, Lu; WOLLER, Kevin R.; WO2011/68899; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, 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 456-64-4, Formula: C7H6F3NO2S

EXAMPLE 50 3-Methyl-2-[5-(trifluoromethanesulfonamido)pentan-1-ylthio]-1,4,7b-triazacyclopent[cd]indene To a solution of 500 mg (1.82 mmol) of 3-methyl-2-[5-(amino)pentan-1-ylthio]-1,4,7b-triazacyclopent[cd]indene in 30 ml of acetonitrile were added 0.51 ml (3.66 mmol) of triethylamine and 1.302 g (3.66 mmol) of N-phenyltrifluoromethanesulfonamide. The mixture was stirred for two hours at room temperature. The solvent was distilled off. To the residue was added methylene chloride, which was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate) to afford 608 mg (82.1%, a pale yellow solid) of the desired compound. NMR(200 MHz,CDCl3)delta: 1.55-1.85(4H,m), 1.97(2H,m), 2.90(3H,s), 3.39(2H,m), 3.50(2H,t,J=7.0 Hz), 7.69(1H,d,J=7.8 Hz), 7.73(1H,d,J=8.0 Hz), 7.95(1H,dd,J=8.0, 7.8 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1,1-Trifluoro-N-phenylmethanesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5958942; (1999); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics