Category: 89501-90-6

Some common heterocyclic compound, 89501-90-6, name is 1-Methyl-1H-pyrazole-3-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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. Quality Control of 1-Methyl-1H-pyrazole-3-sulfonyl chloride

Ui) l-Methyl-lH-pyrazole-3-sulfonic acid benzyl-(l-oxo-l,2,3,4-tetrahydro- isoquinolin-6-yl)-amideTo a stirred solution of 6-benzylamino-3,4-dihydro-2H-isoquinolin-l-one (45 mg, 0.18 mmol) and pyridine (31 mul, 0.39 mmol) in anhydrous acetonitrile (1 ml) was added 1- methyl-lH-pyrazole-3-sulfonyl chloride (70 mg, 0.39 mmol) and the reaction heated to 1500C in a microwave for 0.5 hrs. The solvent was evaporated in vacuo and the crude residue purified by preparative tic (5% methanol in dichloromethane) to afford the title compound as a yellow solid (10 mg, 14%). HPLC retention time 3.83 min. Mass spectrum (ES+) m/z 397 (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 89501-90-6, its application will become more common.

Reference:
Patent; XENTION LIMITED; HAMLYN, Richard, John; MADGE, David; MULLA, Mushtaq; WO2010/139953; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – 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. 89501-90-6, name is 1-Methyl-1H-pyrazole-3-sulfonyl chloride, A new synthetic method of this compound is introduced below., Quality Control of 1-Methyl-1H-pyrazole-3-sulfonyl chloride

General procedure: 0.20 mmol of theappropriately substituted sulfonyl chloride was dissolved in dry pyridine (2mL) and 0.24 mmol of5-amino-7-alkyl-2-[(methylcarbamoyl)amino]-1-benzothiophene-3-carboxamide (19a-c)was added to the solution. The reaction mixture was stirred until the startingamine disappeared completely according to TLC analysis (2-3 hours). 1.0 Mhydrochloric acid was added, the precipitate was filtered off, washed withwater and dried on air. The crude product was dissolved in hot THF (80-100 mL)and decolorized with activated charcoal. The mixture was filtered through celite,washed with ethyl acetate (2 x 40 mL), and the filtrate was evaporated underreduced pressure. The residue was solidified under diisopropyl ether, and theprecipitate was filtered off and dried on air.

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; Gyulavari, Pal; Szokol, Balint; Szabadkai, Istvan; Brauswetter, Diana; Banhegyi, Peter; Varga, Attila; Marko, Peter; Boros, Sandor; Illyes, Eszter; Szantai-Kis, Csaba; Kreko, Marcell; Czudor, Zsofia; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 19; (2018); p. 3265 – 3270;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 89501-90-6, 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 89501-90-6 as follows.

EXAMPLE 5 1-Methylpyrazole-3-sulfonamide A mixture containing chloroform (100 ml), 13.6 g of 1-methylpyrazole-3-sulfonyl chloride and 13.6 g ammonium carbonate was heated to reflux for six hours, cooled, filtered and the solid was washed with water. The water-insoluble solid which was recrystallized from 50% ethanol-water melted at 149-151 and showed absorption peaks in the infrared at 3100 and 3200 cm-1, consistent for the NH2 in the desired product. Anal. Calc. for C4 H7 N3 O2 S: C, 29.8; H, 4.38; N, 26.07; S, 19.9. Found: C, 29.3; H, 4.6; N, 25.3; S, 19.2.

According to the analysis of related databases, 89501-90-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4931081; (1990); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 89501-90-6, 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. 89501-90-6 name is 1-Methyl-1H-pyrazole-3-sulfonyl chloride, 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.

General procedure: 0.20 mmol of theappropriately substituted sulfonyl chloride was dissolved in dry pyridine (2mL) and 0.24 mmol of5-amino-7-alkyl-2-[(methylcarbamoyl)amino]-1-benzothiophene-3-carboxamide (19a-c)was added to the solution. The reaction mixture was stirred until the startingamine disappeared completely according to TLC analysis (2-3 hours). 1.0 Mhydrochloric acid was added, the precipitate was filtered off, washed withwater and dried on air. The crude product was dissolved in hot THF (80-100 mL)and decolorized with activated charcoal. The mixture was filtered through celite,washed with ethyl acetate (2 x 40 mL), and the filtrate was evaporated underreduced pressure. The residue was solidified under diisopropyl ether, and theprecipitate was filtered off and dried on air.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-pyrazole-3-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Article; Gyulavari, Pal; Szokol, Balint; Szabadkai, Istvan; Brauswetter, Diana; Banhegyi, Peter; Varga, Attila; Marko, Peter; Boros, Sandor; Illyes, Eszter; Szantai-Kis, Csaba; Kreko, Marcell; Czudor, Zsofia; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 19; (2018); p. 3265 – 3270;,
Pyrazole – Wikipedia,
Pyrazoles – 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. 89501-90-6, name is 1-Methyl-1H-pyrazole-3-sulfonyl chloride, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H5ClN2O2S

General procedure: 0.20 mmol of theappropriately substituted sulfonyl chloride was dissolved in dry pyridine (2mL) and 0.24 mmol of5-amino-7-alkyl-2-[(methylcarbamoyl)amino]-1-benzothiophene-3-carboxamide (19a-c)was added to the solution. The reaction mixture was stirred until the startingamine disappeared completely according to TLC analysis (2-3 hours). 1.0 Mhydrochloric acid was added, the precipitate was filtered off, washed withwater and dried on air. The crude product was dissolved in hot THF (80-100 mL)and decolorized with activated charcoal. The mixture was filtered through celite,washed with ethyl acetate (2 x 40 mL), and the filtrate was evaporated underreduced pressure. The residue was solidified under diisopropyl ether, and theprecipitate was filtered off and dried on air.

The synthetic route of 89501-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gyulavari, Pal; Szokol, Balint; Szabadkai, Istvan; Brauswetter, Diana; Banhegyi, Peter; Varga, Attila; Marko, Peter; Boros, Sandor; Illyes, Eszter; Szantai-Kis, Csaba; Kreko, Marcell; Czudor, Zsofia; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 19; (2018); p. 3265 – 3270;,
Pyrazole – Wikipedia,
Pyrazoles – 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 89501-90-6 as follows. Formula: C4H5ClN2O2S

Methyl 2-(N-isopropyl-1-methyl-1H-pyrazole-3-sulfonamido)acetate. A 25-niL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 1-methyl-i H-pyrazole-3 – sulfonyl chloride (220 mg, 1.2 mmol), methyl 2-(isopropylamino)-acetate (157 mg, 1.2 mmol), DIPEA (310 mg, 2.4 mmol), DMAP (12 mg, 0.10 mmol), and CH2C12 (10 mL). The mixture was stirred at room temperature for 2 h and concentrated under reduced pressure. The residue was purified by reverse-phase prep-HPLC to afford the title compound (202 mg, 61%) as white solid. MS-ESI:[M+H] 276.1. ?H NMR (500 MHz, CDC13) 3 7.43 (d, J= 2.5 Hz, 1H), 6.74 (d, J= 2.0 Hz, 1H), 4.27-4.24 (m, 1H), 4.02 (s, 2H), 3.99 (s, 3H), 3.77 (s, 3H), 1.09 (d, J= 6.5 Hz, 6H).

According to the analysis of related databases, 89501-90-6, the application of this compound in the production field has become more and more popular.

Reference of 89501-90-6, A common heterocyclic compound, 89501-90-6, name is 1-Methyl-1H-pyrazole-3-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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: A solution of sodium sulfite (17.93g, 142.26 mmol) in H2O (100 ml) was stirred at room temperature for10 min. Sodium carbonate (23.90 g, 284.52 mmol)was added to the stirred solution.The resulting solution was stirred at 50 C for 10 minutes.cyclopropanesulfonyl chloride (20 g, 142.26 mmol) was added dropwise to thesolution and was stirred at 50 C for 2 hours. Thereaction mixture was evaporated to dryness and redissolved in EtOH (200 ml). The suspension was allowed to stir at roomtemperature for 20 min. The suspension was filtered and the filtrate evaporatedto afford a white solid, this was stirred with MeCN (50 ml) and thenfiltered to afford sodium cyclopropanesulfinicacid (13.70 g, 75 %) as a white solid. 1H NMR (400.132 MHz, DMSO d6)delta 1.38-1.31 (m, 1H), 0.27-0.24 (m,2H) and 0.08-0.03 (m, 2H).

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.

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. 89501-90-6, name is 1-Methyl-1H-pyrazole-3-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H5ClN2O2S

To a 50 mL flask was added 1-methyl-1H-pyrazole-3-sulfonyl chloride (1.12g, 6.22 mmol), ethyl (4aS,6S)-6-[(2,4-dimethoxyphenyl)methylaminoj -1 -(4-fluorophenyl)-5 ,6,7,8-tetrahydro-4H- benzo[flindazole-4a-carboxylate (lila) (1.57g, 3.11 mmol), DCM (8 mL), and triethylamine (1.73 mL, 12.45 mmol) successively. After the reaction was stirred at 40C for 5 h, it was directly concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (Si02, 40%-65% EtOAc/hexanes, gradient elution) to provide ethyl (4aS,6S) -6-[(2,4-dimethoxyphenyl)methyl-( 1- methylpyrazol-3 -yl)sulfonyl-aminoj -1 -(4-fluorophenyl)-5 ,6,7, 8-tetrahydro-4H-benzo [flindazole-4a- carboxylate (ilib) (1.86g, 92% yield) as a yellow solid. m/z(ESI, +ve ion) = 650.3 [M+Hj.

According to the analysis of related databases, 89501-90-6, the application of this compound in the production field has become more and more popular.

89501-90-6, name is 1-Methyl-1H-pyrazole-3-sulfonyl chloride, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 89501-90-6

To A solution of 4-[7-tert-butyl-5-(4-chloro-3-fluoro-phenyl)furo[3,2-b]pyridine-2- carbonyl]-3,3-dimethyl-piperazin-2-one (88 mg, 0.1922 mmol) in THF (1.1 mL) was cooled to -78 C and treated with LiHMDS (211 muL of 1 M, 0.211 mmol). The mixture was stirred for 20 min, then a solution of 1-methylpyrazole-3-sulfonyl chloride (41.65 mg, 0.2306 mmol) in THF (88 muL) was added dropwised. The mixture was stirred for 2h at -78C then warmed to rt and was stirred for an extra 4hr. Water was added to the solution and the aqueous phase was extracted 3 times with EtOAc. The combined organic phase was dried over Na2SO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified using reverse phase preperative HPLC affording the title compound after lyophilisation. 4-[7-tert-butyl-5-(4-chloro-3-fluoro-phenyl)furo[3,2- b]pyridine-2-carbonyl]-3,3-dimethyl-1-(2-methylpyrazol-3-yl)sulfonyl-piperazin-2-one (34 mg, 29% yield). ESI-MS m/z calc. 601.1562, found 602.01 (M+1)+; Retention time: 4.34 minutes using method A

Statistics shows that 89501-90-6 is playing an increasingly important role. we look forward to future research findings about 1-Methyl-1H-pyrazole-3-sulfonyl chloride.

89501-90-6, 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. 89501-90-6 name is 1-Methyl-1H-pyrazole-3-sulfonyl chloride, 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.

2-(3-(5-Amino-6-(azetidin-3-yl)pyrazin-2-yl)-4-methylphenyl)-3,3,3-trifluoropropane-1,2-diol hydrochloride salt (0.010 g, 0.025 mmol) in DCM (0.25 mL) was treated with DIPEA (0.026 mL, 0.15 mmol) and 1-methyl-1H-pyrazole-3-sulfonyl chloride (4.5 mg, 0.025 mmol, Maybridge). After 1 hour, the reaction was quenched by the addition of a small quantity of water and ammonium hydroxide solution. The mixture was concentrated via rotary evaporation to remove DCM and the mixture was diluted with MeOH and purified by preparative HPLC-MS (pH=10) to afford the title compound (enriched in one enantiomer, believed to be (S)-, see stereochemical rationale supra) (5 mg, 40%). LCMS calculated for C21H24F3N6O4S (M+H)+: m/z=513.2, found: 513.1. 1H NMR (400 MHz, MeOD) delta 7.93-7.90 (s, 1H), 7.63-7.59 (d, J=2.0 Hz, 1H), 7.59-7.55 (d, J=8.0 Hz, 1H), 7.40-7.35 (m, 2H), 6.84-6.50 (d, J=2.3 Hz, 1H), 4.28-4.24 (m, 4H), 4.14-4.09 (d, J=11.8 Hz, 1H), 4.09-4.05 (d, J=11.8 Hz, 1H), 4.03-3.94 (p, J=8.1 Hz, 1H), 3.56-3.46 (s, 3H), 2.36-2.14 (s, 3H). 19F NMR (376 MHz, MeOD) delta -78.08–78.59 (s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-pyrazole-3-sulfonyl chloride, and friends who are interested can also refer to it.