Month: September 2021

Reference of 55512-05-5,Some common heterocyclic compound, 55512-05-5, name is 3-(Methylsulfonamido)benzaldehyde, molecular formula is C8H9NO3S, 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.

Under argon and at 0 C., 83 mg (0.417 mmol) of N-(3-formylphenyl)methanesulfonamide (Example 86A) were initially charged in 1 ml of abs. tetrahydrofuran. At 0 C., 99 mg (0.833 mmol) of methylmagesium bromide (3 M in diethyl ether) were added dropwise (resulting in the formulation of a precipitate), and the reaction solution was stirred at this temperature for 2 h. The reaction solution was quenched with water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. Yield: 80 mg (89% of theory) LC-MS (Method 8): Rt=1.15 min; MS (ESIpos): m/z=214 [M-H]-.

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

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Vakalopoulos, Alexandros; Meibom, Daniel; Nell, Peter; Sussmeier, Frank; Albrecht-Kupper, Barbara; Zimmermann, Katja; Keldenich, Joerg; Schneider, Dirk; Krenz, Ursula; US2013/210795; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 703-12-8, name is 4-Bromo-N-methylbenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 703-12-8

4-Bromo-N-methylbenzenesulfonamide (100 mg, 0.40 mmol), 5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid (72 mg, 0.48 mmol), potassium fluoride (76 mg, 1.3 mmol), and tris(dibenzylideneacetone)dipalladium(0) (10 mg, 0.01 mmol) were placed in an oven dried flask under nitrogen and dry THF (1.0 mL) was added. Tri-t-butylphosphine (60 muL, 0.02 mmol, 10 wt % in hexane) was added and the reaction was stirred for 16 hours. The reaction mixture was filtered through silica and rinsed with ethyl acetate. The solvent was concentrated in vacuo to provide the crude product. The crude product was pre-adsorbed onto the Celite reagent and purified via Isco chromatography (the Redisep column, silica, gradient 5-50% ethyl acetate in hexane) to afford 4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-N-methylbenzenesulfonamide (28 mg, 25%). MS (ESI) m/z 275. HPLC purity 100.0% at 210-370 nm, 9.0 min.; the Xterra RP18 column, 3.5mu, 150*4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

The synthetic route of 703-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2008/221201; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, 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. name: 4-Bromomethylbenzenesulfonamide

[0498] Ethyl 3-oxo-3-phenylpropanoate (150 mmol) and cesium carbonate (C52CO3, 226 mmol) were dissolved in DMSO (50 ml). The reaction mixture was stirred at rt for 10 minutes at which time potassium iodide were added (KI, 150 mmol) and 4-(bromomethyl)- benzenesulfonamides (165 mmol). The resulting mixture was stirred at rt for 1 h. Upon completion as detected by LCMS, the reaction mixture was diluted with a large excess of ethyl acetate and filtered through celite. The filtrate was washed with 1 M HC1, sat aq NH4C1 and brine, dried over Na2504, filtered, and concetrated under reduced pressure. The residue was purified directly on silica using gradient elution (20-40 percent ethyl acetate in hexanes over 16 CV).

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

Reference:
Patent; THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; VANDERBILT UNIVERSITY; MALONEY, David J.; JADHAV, Ajit; BANTUKALLU, Ganesha Rai; BRIMACOMBE, Kyle Ryan; MOTT, Bryan T.; YANG, Shyh Ming; URBAN, Daniel Jason; HU, Xin; SIMEONOV, Anton; KOUZNETSOVA, Jennifer L.; WATERSON, Alex Gregory; SULIKOWSKI, Gary Allen; KIM, Kwangho; CHRISTOV, Plamen; JANA, Somnath; (387 pag.)WO2016/109559; (2016); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 57561-39-4, A common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, molecular formula is C8H17NO3, 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.

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Example 1 and ethyl acetate (20 mL) were added pyridine (0.97 mL) and 4-dimethylaminopyridine (catalytic amount), and ethyl chlorocarbonate (1.25 mL) was dropwise added. The mixture was stirred overnight at room temperature and ethyl acetate (50 mL) was added. The mixture was washed with water (50 mL), a 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, a 4N hydrogen chloride – ethyl acetate solution (10 mL) was added to the residue. After stirring at room temperature for 2 hrs., diethyl ether (10 mL) was added, and the precipitated solid was collected by filtration. The solid was dried under reduced pressure to give the title compound (1.66 g) as a white solid.1H-NMR(DMSO-d6) : 1.23(3H,t,J=7.1Hz), 2.54 (3H,s), 3.16-3.22(2H,m), 4.15(2H,q,J=7.1Hz), 4.32-4.37(2H,m), 9.25 (2H,br).

The synthetic route of 57561-39-4 has been constantly updated, and we look forward to future research findings.

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

Adding a certain compound to certain chemical reactions, such as: 154748-63-7, name is tert-Butyl (3-hydroxycyclobutyl)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 154748-63-7, name: tert-Butyl (3-hydroxycyclobutyl)carbamate

c) tert-butyl (3-tosyl-cyclobutyl)-carbamate18.7 g (100 mmol) tert-butyl (3-hydroxy-cyclobutyl)-carbamate and 12.1 g (120 mmol) triethylamine are placed in 500 mL chloroform. 20.5 g (105 mmol) tosyl chloride, which is dissolved in 150 mL chloroform, is added dropwise to this solution at 00C with stirring. Then the reaction mixture is allowed to come up to 200C and stirred for a further 2 h. The organic phase is washed successively with water, with dilute hydrochloric acid, with sodium hydrogen carbonate solution and again with water. The organic phase is dried on magnesium sulphate and the solvent is eliminated in vacuo. Yield: 28.3 g MS (ESI): 342 (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 (3-hydroxycyclobutyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2007/115999; (2007); A1;,
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. 354-38-1, name is 2,2,2-Trifluoroacetamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C2H2F3NO

Intermediate 186 (0.43 g, 1.22 mmol) was dissolved in DCM (20 mL) and 2,2,2- trifluroacetamide (0.28 g, 2.49 mmol), magnesium oxide (0.21 g, 5.1 mmol), rhodium(II) acetate dimer (0.028 g, 0.064 mmol) and iodobenzene I,I-diacetate (0.53 g, 1.65 mmol) were added. After 18 h at r.t. the pink solution was filtered through a pad of celite and concentrated in vacuo. The residue was purified by column chromatography (Si02, 20- 60% EtOAc:DCM) to yield the title compound (0.39 g, 90%). HPLC-MS : MH+ mlz 431 , RT 2.00 minutes

According to the analysis of related databases, 354-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHOVATIA, Prafulkumar Tulshibhai; FOULKES, Gregory; JOHNSON, James Andrew; JONES, Severine Danielle; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LOKE, Pui Leng; LOWE, Martin Alexander; MANDAL, Ajay; NORMAN, Timothy John; PALMER, Christopher Francis; PEREZ-FUERTES, Yolanda; PORTER, John Robert; SMYTH, Donald; TRANI, Giancarlo; UDDIN, Muhammed; ZHU, Zhaoning; (207 pag.)WO2016/198400; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 194920-62-2, name is tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate, molecular formula is C15H32N2O5, 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. Product Details of 194920-62-2

To a 25 mL round bottomed flask equipped with a magnetic stir bar, rubber septum, and argon inlet containing tert-butyl 3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propylcarbamate (amine, 160 mg, 0.5 mmol), 2-azidoacetic acid (56 mg, 0.55 mmol, in 50% DCM solution), NaHCO3 (168 mg, 2 mmol), and 1 mL DMF was added EDC (115 mg, 0.6 mmol). The mixture was stirred at rt for 3 h and concentrated in vacuo. The crude product was purified by silica chromatography (gradient 5% to 90% EtOAc in hexane) to afford compound 141 as a clear oil (130 mg, 65%). MS(ESI) m/z 426 (M+Na+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 194920-62-2, its application will become more common.

Reference:
Patent; SIEMENS MEDICAL SOLUTIONS USA, INC.; WO2008/124703; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 22117-85-7, name is 2-Methoxy-5-sulfamoylbenzoic acid, I believe this compound will play a more active role in future production and life. 22117-85-7

example 35 by following general method D using 0.84 g. of 6-methoxy-3-sulfamoylbenzoic acid and 0.6 g. of N-benzyl-N-methylethylenediamine, 1.2 g. of N-[2-(N’-benzyl-N’-methylamino)ethyl]-6-methoxy-3-sulfamoylbenzamide was obtained. Melting point: 202-203 C. (recrystallized from a mixture of methanol and isopropanol). Elemental analysis for C18 H23 N3 O4 S:

The chemical industry reduces the impact on the environment during synthesis 22117-85-7. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US4097487; (1978); A;,
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. 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 63920-73-0

This product was used in next step without further purification. To a solution of 2-dimethylaminomethyl-1H-indole-5-carbaldehyde (0.88 g crude, 4.35 mmol) and 2-amino-4,6-dimethoxy-benzamide (0.85 g, 4.35 mmol) in N,N-dimethylacetamide (15 mL) were added sodium hydrogen sulfite (58.5 wt %, 0.95 g, 5.22 mmol) and p-toluenesulfonic acid (0.99 g, 5.22 mmol). The reaction mixture was stirred at 120 C. for 5 hours under nitrogen, then cooled to room temperature, and concentrated under reduced pressure. 30% aqueous sodium carbonate (50 mL) was then added. The separated solid was filtered, washed with water (50 mL), and dried under vacuum. Crude compound was purified by the Simpliflash system (0-5% methanol in CH2Cl2 and 7 N ammonia in methanol 5% in CH2Cl2 as eluent) to give the title compound as an off-white solid. Yield: 0.83 g (50%). MP 187-188 C. 1H NMR (400 MHz, DMSO-d6): delta 11.82 (s, 1H), 11.34 (s, 1H), 8.38 (s, 1H), 7.93 (d, J=8.59 Hz, 1H), 7.40 (d, J=8.59 Hz, 1H), 6.73 (s, 1H), 6.49 (s, 1H), 6.40 (s, 1H), 3.90 (s, 3H), 3.85 (s, 3H), 3.57 (s, 2H), 2.21 (s, 6H)

According to the analysis of related databases, 63920-73-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281399; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 121-30-2, These common heterocyclic compound, 121-30-2, name is 4-Amino-6-chlorobenzene-1,3-disulfonamide, 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.

To a solution of aminoacetaldehyde dimethylacetal (2.18 mL, 2.13 g, 20.2 mmol) in EtOAc (25 mL) at 0 C. was added dropwise a solution of HCl in ether (13 mL, 2N solution in ether). The mixture was stirred at 0 C. for 5 minutes. To this solution, 4-chloro-6-aminobenzene-1,3-disulfonamide (Aldrich, 5.8 g, 20.3 mmol) in diethylene glycol dimethylether (30 mL) was added. The reaction mixture was then heated at 60-90 C. for 1 hour. The solvent was decanted and the solid was dissolved in water. An aqueous solution of Na2CO3 (10%) was added to adjust the pH 7-8, extracted with EtOAc, dried over Na2SO4, filtered and the solvent was evaporated. The crude material was chromatographed on silica gel eluting with CH2Cl2:EtOAc:MeOH (1:1:0.2 to 1:1:1) to give the title compound (3 g, 53% yield) as a white solid: mp 157-160 C. 1H NMR (400 MHz, d6-DMSO) delta 7.97 (s, 1H), 7.05 (s, 1H), 5.65-4.70 (m, 1H), 2.88-2.96 (m, 1H), 2.77-2.84 (m, 1H); 13C NMR (100 MHz, d6-DMSO) delta 147.1, 134.8, 128.4, 125.9, 118.7, 117.6, 68.1, 44.9. Mass spectrum (API-TIS) m/z 325 (M-H), 327 (MH+); Anal. calcd for C8H11ClN4O4S20: C, 30.06; H, 3.54; N, 16.70. Found: C, 30.26; H, 3.40; N, 16.38.

Statistics shows that 4-Amino-6-chlorobenzene-1,3-disulfonamide is playing an increasingly important role. we look forward to future research findings about 121-30-2.

Reference:
Patent; NitroMed, Inc.; US2006/189603; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics