Category: 137049-00-4

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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methyl-1H-imidazole-4-sulfonyl chloride

Intermediate example 1-84 (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl l-methyl-lH-imidazole-4- sulfonateTo a solution of (35)-3-(dibenzylamino)chroman-5-ol (300 mg, 0.87 mmol, described in WO9914212A1) in acetonitrile (10 mL) was triethylamine (0.363 mL, 2.61 mmol) and 1- methyl-leta-imidazole-4-sulfonyl chloride (173 mg, 0.96 mmol) added and the reaction mixture was stirred at ambient temperature over night. The reaction mixture was concentrated in vacuo and purified by column chromatography using a gradient of ethyl acetate in heptane to yield 375 mg (88 %); 1H NMR (400 MHz, DMSO-J6) delta ppm 8.06 (d, 1 H), 7.93 (d, 1 H), 7.30 – 7.42 (m, 8 H), 7.18 – 7.27 (m, 2 H), 7.06 (t, 1 H), 6.69 (dd, 1 H), 6.62 (dd, 1 H), 4.17 – 4.31 (m, 1 H), 3.97 (t, 1 H), 3.61 – 3.73 (m, 7 H), 2.84 – 2.99 (m, 2 H), 2.63 – 2.75 (m, 1 H); MS (ESI) m/z 490 [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 137049-00-4.

Reference:
Patent; ASTRAZENECA AB; WO2008/130319; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, A new synthetic method of this compound is introduced below., COA of Formula: C4H5ClN2O2S

General procedure: The amino phenyl derivative (0.4 mmol, 1 equiv) was dissolvedin pyridine absolute (3 mL) and was spiked with sulfonyl chloride/acid chloride (1.5 equiv). The reaction mixture was stirred overnightat rt (refluxed in case of amide coupling). The reaction wasquenched by adding 10 mL of 2 N HCl and extracted with ethylacetate (3 50 mL). The organic layers werewashed with saturatedNaHCO3 (50 mL) and brine (50 mL), dried over magnesium sulfate,filtered and concentrated to dryness. The product was purified byCC. The title compound was prepared by reaction of (5-(3-aminophenyl)thiophene-2-yl)(2,6-difluoro-3-hydroxyphenyl)methanone (30)(100 mg, 0.30 mmol) and 1-methyl-1H-imidazole-4-sulfonyl chloride (81 mg, 0.45mmol) according to Method C. The product was purified by CC (dichloromethane/methanol95:5); yield: 72% (103 mg). 1H NMR (500 MHz, acetone-d6)delta 9.17 (s, 1H), 9.01 (s, 1H), 7.75-7.72 (m, 2H), 7.64-7.61 (m, 2H), 7.54 (d, J= 4.1 Hz, 1H), 7.50-7.43 (m, 1H),7.39-7.34 (m, 2H), 7.21 (td, J= 9.4, 5.5 Hz, 1H), 7.04 (td, J= 8.8, 1.9Hz, 1H), 3.76 (s, 3H);13C NMR (125 MHz, acetone-d6) delta 180.7, 155.1, 153.6,151.6, 149.5, 147.5, 143.3, 142.7, 140.7, 140.1, 138.3, 134.5, 130.9, 126.2,122.5, 121.9, 120.4, 118.4, 112.6, 112.4, 34.2; MS (ESI): 476.21 (M+H)+)+; HPLC purity ? 98% (Rt = 12.54 min).

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; Abdelsamie, Ahmed S.; Bey, Emmanuel; Gargano, Emanuele M.; Van Koppen, Chris J.; Empting, Martin; Frotscher, Martin; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 56 – 68;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 137049-00-4,Some common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-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.

3. Synthesis of (1-(1-Methyl-1H-Imidazol-4-ylsulfonyl)Piperidin-4-yl)(Phenyl)Methanone, 4; To a solution of 4-benzoylpiperidine hydrochloride (1.50 g, 6.64 mmol) and DIPEA (2.74 mL, 15.3 mmol) in CH2Cl2 (35 mL) was added 1-methylimidazole-4-sulfonyl chloride (1.31 g, 7.31 mmol) and stirred for 18 h. The reaction was washed with 2 N NaOH (30 mL), dried over MgSO4 and concentrated under vacuum to afford 4 as a white solid (2.05 g, 93%); 1H-nmr (400 MHz, CDCl3) delta 7.81-7.78 (m, 2H), 7.52-7.36 (m, 5H), 3.86-3.78 (m, 2H), 3.71 (s, 3H), 3.26-3.17 (m, 1H), 2.82 (td, J=11.0, 3.0 Hz, 2H), 1.92-1.84 (m, 4H); m/z 334.0 [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 1-Methyl-1H-imidazole-4-sulfonyl chloride, its application will become more common.

Reference of 137049-00-4, The chemical industry reduces the impact on the environment during synthesis 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, I believe this compound will play a more active role in future production and life.

Intermediate 27 (40 mg, 79 mumol) was dissolved in 1 mL of pyridine and flushed with nitrogen, It was cold to 0 C. and added 1-methyl-1 H-imidazole-4-sulfonyl chloride (43,mg, 240 mumol). The mixture was allowed to warm to room temperature and stirred for 20 h under nitrogen. The reaction was diluted with 10 mL of EtOAc, washed with brine, dried over Na2SO4 and concentrated in vacuum to give crude product which was then purified by flash chromatography on silica gel (20% to 50% ethyl acetate in hexane, then 5/5/1 of EtOAc/hexane/MeOH) to provide 55 (24 mg, 47%). m/z=648 (M+1). The deprotection of the DPM group at C8-OH was carried out as in the conversion of 28 to 29. The resulting residue was then purified by reverse-phase prep HPLC to provide 13 mg (59% in yield) of 56 as a TFA salt. 300 MHz 1H NMR (CDCl3) delta (ppm): 9.0 (d, 1H); 8.4 (d, 1H); 7.5 (m, 1H); 7.4 (s, 1H); 7.3 (m, 2H); 7.2 (s, 1H); 7.0 (t, 2H); 4.8 (s, 2H); 4.3-4.5 (m, 2H); 3.6 (s, 3H); 3.4 (s, 3H). m/z=482 (M +1).

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, 1-Methyl-1H-imidazole-4-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Some common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-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. name: 1-Methyl-1H-imidazole-4-sulfonyl chloride

Example 227 1-methyl-N-[3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-phenoxyphenyl]-1H-imidazole-4-sulfonamide [1006] The product from Example 225C (0.044 g, 0.15 mmol), 1-methyl-1H-imidazole-4-sulfonyl chloride (0.033 g, 0.180 mmol) and triethylamine (0.042 mL, 0.30 mmol) were combined in dichloromethane (0.75 mL), heated at 60 C. for 2 hours and concentrated. Purification by chromatography (silica gel, 0-3% methanol in dichloromethane) afforded the title compound (0.038 g, 56%). 1H NMR (300 MHz, DMSO-d6) delta 10.21 (s, 1H) 7.84 (d, J=1.36 Hz, 1H) 7.75-7.78 (m, 2H) 7.48 (dd, J=9.49, 2.71 Hz, 1H) 7.25-7.35 (m, 2H) 7.21 (d, J=2.71 Hz, 1H) 7.09 (dd, J=8.82, 2.71 Hz, 1H) 7.03 (t, J=7.46 Hz, 1H) 6.89 (d, J=8.82 Hz, 1H) 6.83 (d, J=7.80 Hz, 2H) 6.37 (d, J=9.49 Hz, 1H) 3.67 (s, 3H) 3.43 (s, 3H). MS (ESI+) m/z 437 (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 137049-00-4, its application will become more common.

Reference:
Patent; HUBBARD, Robert D.; WANG, Le; PARK, Chang H.; SUN, Chaohong; McDANIEL, Keith F.; PRATT, John K.; SOLTWEDEL, Todd N.; WENDT, Michael D.; HOLMS, John H.; LIU, Dachun; SHEPPARD, George S.; US2013/331382; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 137049-00-4, 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. 137049-00-4 name is 1-Methyl-1H-imidazole-4-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.

0.07 g (0.21 mmol) of (R,3r)-3-((7S,8R)-7-(azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclobutanamine were dissolved in dichloromethane, 0.05 g (0.41 mmol) dimethylaminopyridine were added, followed by 0.04 g (0.21 mmol) of 1-methyl-1H-imidazole-4-sulfonyl chloride. The mixture was stirred at room temperature overnight. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and aqueous bicarbonate solution. The aqueous phase was discarded and the organic phase was washed again with aqueous bicarbonate solution, then twice with aqueous ammoniumchloride solution (10%). The organic phase was dried over MgSO4 and evaporated to dryness. The desired product was obtained as a light brown resin (0.01 g, 0.01 mmol, 7%). ESI-MS [M+H+]=491 Calculated for C28H34N4O2S=490.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-imidazole-4-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; Amberg, Wilhelm; Pohlki, Frauke; Lange, Udo; Wang, Ying; Brewer, Jason; Vasudevan, Anil; Lao, Yanbin; Hutchins, Charles; Zhao, Hongyu; Li, Huan-Qiu; US2015/111875; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-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. Recommanded Product: 1-Methyl-1H-imidazole-4-sulfonyl chloride

2.2 Ethyl 1-(3,4-dichlorobenzyl)-7-(2-(1-methyl-1 H-imidazole-4-sulfonamido)ethoxy)- 1 ,2,3,4-tetrahydronaphthalen-2-ylcarbamate; Ethyl 7-(2-aminoethoxy)-1 -(3,4-dichlorobenzyl)-1 ,2,3,4-tetrahydronaphthalen-2- ylcarbamate hydrochloride (100 mg, 0.229 mmol) and DMAP (27.9 mg, 0.229 mmol) were dissolved in CH2CI2 (15 ml) and 1-methyl-1 H-imidazole-4-sulfonyl chloride (41.3 mg, 0.229 mmol) dissolved in CH2CI2 (15 ml) was added. The reaction mixture was stirred over night at RT. After addition of H2O the phases were separated and the aqueous phase was extracted with CH2CI2. The organic layer was washed with HCI (1 N), NaHCO3 solution and NaCI solution, then dried on MgSO4 and the solvent was removed. To the residue EtOAc/ diethylether (1 :1 ) was added, stirred, and the precipitate was separated by filtration to obtain a brown solid of product (100 mg). ESI-MS [M+H+] = 581.5 Calculated for C26H30CI2N4O5S = 580.13

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 137049-00-4, its application will become more common.

Reference:
Patent; ABBOTT GMBH &; CO. KG; AMBERG, Wilhelm; OCHSE, Michael; LANGE, Udo; KLING, Andreas; BEHL, Berthold; HORNBERGER, Wilfried; MEZLER, Mario; HUTCHINS, Charles; WO2010/92180; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 137049-00-4

To a solution of intermediate 2.40 (20. mg, 0.078 mmol) and triethylamine (30 muL, 0.2 mmol) in dichloromethane (0.5 mL) at ambient temperature was added 1-methyl- 1H-imidazole-4-sulfonyl chloride (21 mg, 0.12 mmol). The resulting mixture was stirred for 18 h, then diluted with wet dimethyl sulfoxide (0.5 mL), filtered through Celite and purified via mass-directed isolation using ultra-performance liquid chromatography (21 mg, 68% yield).1H NMR (500 MHz, Acetonitrile-d3) d 8.64 (s, 1H), 7.70 (dd, J = 11.8, 2.4 Hz, 1H), 7.62 (d, J = 1.4 Hz, 1H), 7.54 (d, J = 1.4 Hz, 1H), 7.37 (t, J = 8.6 Hz, 1H), 7.22 (ddd, J = 8.8, 2.4, 1.2 Hz, 1H), 3.80 (ddd, J = 11.7, 3.7, 1.9 Hz, 1H), 3.71 (s, 3H), 3.63 (d, J = 12.1 Hz, 1H), 2.65 (t, J = 11.1 Hz, 1H), 2.58 (ddt, J = 10.8, 7.2, 3.5 Hz, 1H), 2.52 (td, J = 11.9, 3.0 Hz, 1H), 1.93- 1.89 (m, 1H), 1.85- 1.74 (m, 1H), 1.65- 1.52 (m, 1H), 1.52- 1.39 (m, 1H); AMM (ESI) m/z 401.0858 [calc for C16H19ClFN4O3S (M+H)+ 401.0850].

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; VAL-CHUM, LIMITED PARTNERSHIP; GRENIER, Melissa Carey; SMITH, Amos B., III; FINZI, Andres; DING, Shilei; CHAPLEAU, Jean-Philippe; (240 pag.)WO2020/28482; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 137049-00-4, 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 137049-00-4 as follows.

To a solution of 2-chloro-1-(1 /-/-indol-3-yl)-2-phenylethanone (0.200 g; 0.741 mmol) in DMF (5 mL) cooled to 0 C was added sodium hydride (60% dispersion in mineral oil; 0.053 g; 1.333 mmol). The reaction mixture was stirred at room temperature for 0.5 h. 1-Methyl-1 H- imidazole-4-sulfonyl chloride (0.268 g; 1.484 mmol) and DMAP (0.005 g; 0.037 mmol) were added and the reaction mixture was stirred at room temperature for 3 h. Water was added and the reaction mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (30% to 100%) in heptane furnished 0.301 g (98%) of 2-chloro-1-(1-((1-methyl-1 /-/-imidazol-4-yl)sulfonyl)-1 H-indol- 3-yl)-2-phenylethanone as a solid. ESI/APCI(+): 414 (M+H); 436 (M+Na). ESI/APCI(-): 412 (M- H).

According to the analysis of related databases, 137049-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim; WO2013/45516; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 137049-00-4

General procedure: 2-Aminoethyl amine (1 equiv.) and 2-trifluormethyl-4-fluoro benzonitrile(1 equiv.) were dissolved under argon in dry MeCN, followedby addition of Et3N (1.5 equiv). The resulting reaction mixture wasstirred at 50 C for 4 h. After cooling to room temperature water andCH2Cl2 were added, followed by thorough extraction. The combinedorganic layer was dried over Na2SO4, filtered and concentrated underreduced pressure to afford desired 4-[(2-aminoethyl)-amino]-2-(trifluormethyl)benzonitrile. 4-[(2-aminoethyl)-amino]-2-(trifluormethyl)benzonitrile (160 mg, 0.69 mmol) was dissolved in a flame-dried roundbottomedflask in CH2Cl2 (20 mL) under argon and diisopropylethylamine (0.37 mL, 2.09 mmol) was added. After stirring at room temperaturefor 5 min a solution of the corresponding aryl- or hetarylsulfonylchloride (0.69 mmol) in dry CH2Cl2 (5 mL) was added, andthe resulting reaction mixture was stirred at room temperature for20 h¡¤H2O and CH2Cl2 were added, followed by thorough extraction. Thecombined organic layer was dried over Na2SO4, filtered, concentratedunder reduced pressure and purified via column chromatography(heptane/EtOAc, gradient 10:0 to 1:1) to afford desired N-(2-{[4-cyano-3-(trifluormethyl)phenyl]amino}-ethyl)-aryl-/hetaryl sulfonamide 9i-z.

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Frackenpohl, Jens; Schneider, Linn; Decker, Luka J.B.; Dittgen, Jan; Fenkl, Franz; Fischer, Christian; Franke, Jana; Freigang, Joerg; Getachew, Rahel; Gonzalez Fernandez-Nino, Susana M.; Helmke, Hendrik; Hills, Martin J.; Hohmann, Sabine; Kleemann, Jochen; Kurowski, Karoline; Lange, Gudrun; Luemmen, Peter; Meyering, Nicole; Poree, Fabien; Schmutzler, Dirk; Wrede, Sebastian; Bioorganic and Medicinal Chemistry; vol. 27; 24; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem