Category: 137049-00-4

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.

To a solution of l-N-Boc-3-cyanoazetidine (5.0 g, 27.5 mmol) in 1,4- dioxane (50 mL) was added 4 N HCl (50 mL) and stirred for 2 h. The reaction was concentrated under vacuum. The residue was dissolved in CH2Cl2 (60 mL) and DIPEA (10.6 mL, 60.4 mmol) and added l-methylimidazole-4-sulfonyl chloride (4.94 g, 27.5 mmol) and stirred at room temperature for 20 h. The reaction mixture was washed with 2 N NaOH (50 mL), dried over MgSO4 and concentrated under vacuum to afford 8 as a white crystalline solid (4.97 g, 80%); ; Eta-nmr (300 MHz, CDCl3) delta 7.06 (s, IH), 7.56 (s, IH), 4.27-4.19 (m, 4H), 3.82 (s, 3H), 3.43-3.31 (m, IH); LC-MS (214) 99%, 0.93 min, m/z 227 ‘.1 (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:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig, W.; CONN, P., Jeffrey; WILLIAMS, Richard; JONES, Carrie, K.; SHEFFLER, Douglas, J.; WO2010/114907; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 137049-00-4, These common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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: To an 93 (R)-N-methyl-N-(pyrrolidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 5aa (70.0mg, 0.322mmol) solution in 1.00mL of 119 dichloromethane in a 5mL round-bottom flask, 151 methanesulfonyl chloride (36.9mg, 0.322mmol) and 121 N,N-diisopropylethylamine (0.0590mL, 0.339mmol) were added. Then, the reaction solution was stirred at room temperature overnight before being concentrated under reduced pressure. The residue was purified by flash column chromatography (methanol: dichloromethane=2:98).

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

Reference:
Article; Chough, Chieyeon; Joung, Misuk; Lee, Sunmin; Lee, Jaemin; Kim, Jong Hoon; Kim, B. Moon; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1495 – 1510;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference 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.

Example 144 (+-)-N-Benzyl-trans-3,4-dimethyl-4-(3-(1-methyl-1H-imidazole-4-sulfonylamino)phenyl)piperidine To a solution of (+-)4-(3-aminophenyl)-N-benzyl-trans-3,4-dimethylpiperidine (Preparation 9, 500 mg, 1.706 mmol) in pyridine (7 ml) under nitrogen was added 1-methyl-1H-imidazole-4-sulfonyl chloride (462 mg, 2.56 mmol), and the resultant mixture was stirred for 52 h before hydrolysing with ice (10 g). The reaction mixture was concentrated in vacuo at 80 C. and the residue was taken up in dichloromethane (200 ml), washed with saturated aqueous sodium hydrogen carbonate solution (70 ml), dried (Na2SO4), filtered and concentrated in vacuo to give the crude product. This was purified by silica (10 g) column chromatography eluding with ethyl acetate:triethylamine (99:1) to give the title compound as a white solid (640 mg, 86%). NMR (CDCl3, selected data for the free base): 0.5 (d, 3H), 1.1 (s, 3H), 3.6 (s, 3H), 6.8-7.4 (m, 11H). MS (thermospray): M/Z [MH+] 439.1; C24H30N4O2S+H requires 439.2.

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; Armer, Richard Edward; Dutton, Christopher James; Gethin, David Morris; Gibson, Stephen Paul; Smith, Julian Duncan; Tommasini, Ivan; US2003/78282; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 137049-00-4, A common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-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.

Step 4A: To a stirred solution of (3i?)-l-[4-fluoro-2-(trifluoromethyl)phenyl]-3- methylpiperazine (1.038 g, 3.96 mmol) and diisopropylethylamine (1.38 rnL, 7.92 mmol) in anhydrous dichloromethane (15 rnL) was added 1 -methyl- lEta-imidazole-4-sulfonyl chloride (0.715 g, 3.96 mmol) at O0C. The mixture was stirred at O0C for 30 min, then stirred at room temperature for o/n. The reaction mixture was washed with H2O, extracted with DCM. The organic layer was dried over Na2SO4 and concentrated. The crude product was purified via flash column chromatography, eluting with 2-4% MeOH/DCM to yield (2i?)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methyl-l-[(l- methyl-lH-imidazol-4-yl)sulfonyl]piperazine as a light yellow solid (1.22 g, 75.8% yield).

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

Reference:
Patent; WYETH LLC; WAN, Zhao-Kui; CHENAIL, Eva; IPEK, Manus; LI, Huan-Qiu; MANSOUR, Tarek, Suhayl; SURI, Vipin; XIANG, Jason, Shaoyun; SAIAH, Eddine; WO2010/141550; (2010); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 137049-00-4, A common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-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.

To a solution of tert-butyl (6-(3-((6-amino-,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)oxy)-5-propoxyphenoxy)hexyl)carbamate (67 mg, 0.12 mmol) in DCM (2 ml) were added 1-methyl-1H-imidazole-4-sulfonyl chloride (46 mg, 0.26 mmol) and pyridine (100 muL, 1.24 mmol), the sulfonyl chloride was not fully soluble, so dioxanes (2 mL) was added and the resulting mixture was stirred at 60 C. for 21 h. The resulting suspension was concentrated, then purified by silica-gel chromatography (1:5-1:1 EtOAc/hexanes then 100% EtOAc) and dried to give tert-butyl (6-(3-((1,3-dimethyl-6-(1-methyl-1H-imidazole-4-sulfonamido)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)oxy)-5-propoxyphenoxy)hexyl)carbamate as a red-colored amorphous solid (58 mg, 68%). MS (ES+) C33H46N6O8S requires: 686. found 687 [M+H]+. 1H NMR (600 MHz, CDCl3) delta: 7.97 (br-s, 1H), 7.60 (s, 1H, overlapped with CHCl3), 7.35 (s, 1H), 7.31 (s, 1H), 7.20 (s, 1H), 6.57 (s, 1H), 6.14 (s, 1H), 5.77 (br-s, 1H), 5.72 (br-s, 1H), 3.86 (t, J=6.4 Hz, 2H), 3.83 (t, J=6.5 Hz, 2H), 3.62 (s, 3H), 3.45 (s, 3H), 3.31 (s, 3H), 3.12 (br-t, J=6.3 Hz, 2H), 1.76 (m, 4H), 1.51 (m, 2H), 1.46 (m, 2H), 1.44 (s, 9H), 1.37 (m, 2H), 1.01 (t, J=7.3 Hz, 3H).

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; Board of Regents, The University of Texas System; Palmer, Wylie; Jones, Philip; Liu, Gang; Petrocchi, Alessia; Reyna, Naphtali; Subrumanian, Govindan; Theroff, Jay; Yau, Anne; (114 pag.)US2016/60260; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 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.

Vi) l-Methyl-lH-imidazole-4-sulfonic acid (4-chloro-benzyl)-(2-ethyl-4,4-dimeihyl- l-oxo-l,2,3,4-tetrahydro-isoquinolin-7-yl)-amideTo a stirred solution of 7-(4-chloro-benzylamino)-2-ethyl-4,4-dimethyl-3,4-dihydro-2H-isoquinolin-l-one (17 mg, 0.05 mmol) and pyridine (9 mul, 0.11 mmol) in anhydrous acetonitrile (1 ml) was added 1 -methyl- lH-imidazole-4-sulfonyl chloride (20 mg, 0.11 mmol) and the reaction heated to 150C 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 colourless solid (5 mg, 21%). HPLC retention time 4.42 min. Mass spectrum (ES+) m/z 487 (M+H).

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

Reference:
Patent; XENTION LIMITED; HAMLYN, Richard, John; MADGE, David; MULLA, Mushtaq; WO2010/139953; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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., Formula: C4H5ClN2O2S

General procedure: NaH (6.7 mg, 0.28 mmol) was suspended in dry DMF.6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-b]pyridine (39, 50 mg, 0.25 mmol) was added intothe above solution slowly at 0 C. Then, the cooling solution was stirred for 0.5 h. Subsequently,6-chloroimidazo[2,1-b]thiazole-5-sulfonyl chloride (77 mg, 0.3 mmol) was added and stirred for another 4 h at room temperature. Then, water (30 mL) was added to the reaction system. The reactionmixture was extracted with ethyl acetate (3 40 mL). The combined organic phase was washed withsaturated salt water (3 40 mL), dried over anhydrous Na2SO4, filtered, and concentrated underreduced pressure to give the corresponding crude target product, which was purified by flash columnchromatography with dichloromethane/methanol to afford compound 5 as a white hairy solid withthe yield of 78%.

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:
Article; Jiang, Alan; Liu, Qiufeng; Wang, Ruifeng; Wei, Peng; Dai, Yang; Wang, Xin; Xu, Yechun; Ma, Yuchi; Ai, Jing; Shen, Jingkang; Ding, Jian; Xiong, Bing; Molecules; vol. 23; 3; (2018);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 137049-00-4, A common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-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.

To Example 242 B (12.74 g, 57.1 mmol) in 15 mL of dichloromethane were added triethylamine (12.13 g, 120 mmol) and 4-dimethylaminopyridine (0.35 g, 2.85 mmol). The reactionmixture was cooled to 0 C. 1 -methyl- lH-imidazole-4-sulfonyl chloride (10.82 g, 59.9 mmol) was added portion wise at 0 C. The reaction mixture was slowly warmed up to room temperature and stirred for 1 hour. The reaction mixture was partitioned with dichloromethane, and water. The organic fraction was collected, washed with water, concentrated, and purified by flash- chromatography on silica gel (100% ethyl acetate) to afford the title compound. MS (ESI) m/z 368.0 (M+H)+.

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

Reference:
Patent; ABBVIE DEUTSCHLAND GMBH & CO. KG; ABBVIE INC.; AMBERG, Wilhelm; POHLKI, Frauke; LANGE, Udo; WANG, Ying X.; ZHAO, Hongyu H.; LI, Huan-Qiu; BREWER, Jason T.; ZANZE, Irini; DIETRICH, Justin; VASUDEVAN, Anil; DJURIC, Stevan, W.; LAO, Yanbin; HUTCHINS, Charles W.; WO2014/140310; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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., COA of Formula: C4H5ClN2O2S

To a solution of tert-butyl 8-amino-5-(ethylsulfonyl)-1,3,4,5-tetrahydro-2H- pyrido[4,3-b]indole-2-carboxylate (0.26 mmol) in dry dichloromethane (8 mL) was added 1-methyl-1H-imidazole-4-sulfonyl chloride (0.32 mmol) followed by triethyl amine (0.52 mmol), the reaction mixture was stirred at room temperature for overnight and diluted with dichloromethane (20 mL), washed with saturated NaHCO3 solution (10 mL), dried over Na2SO4. The solution was concentrated in vacuo and the EPO crude product was used for the next step without farther purification. MS (M+l): 524.0.

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; WO2006/101434; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, belongs to imidazoles-derivatives 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 137049-00-4, HPLC of Formula: C4H5ClN2O2S

(1-Methylimidazol-4-yl)sulfonyl chloride (23 mg, 0.13 mmol) was added dropwise to a stirred solution of 3-[4-(2-ethyl-5-methyl-2H-pyrazol-3-yl)piperidin-1-yl]-1-phenylpropylamine (see Example 8) (48 mg, 0.15 mmol) and Et3N (20 muL, 0.14 mmol) in CH2Cl2 (2 mL) at RT under N2. The mixture was stirred for 18 h, then was diluted with CH2Cl2 (20 mL) and washed with NaHCO3 solution (20 mL). Then the organic layer was separated and the aqueous phase was re-extracted with CH2Cl2 (20 mL) and the combined organic extracts dried (MgSO4), and concentrated under reduced pressure. The residue was taken up in Et2O (5 mL) and purified by trituration. The title compound (55 mg, 56%) was isolated as a colourless solid. 1H NMR (d6-DMSO, 400 MHz) delta8.28 (1H, d, J=7.8 Hz), 7.68 (1H, s), 7.54 (1H, s), 7.26-7.14 (5H, m), 5.81 (1H, s), 4.35-4.25 (1H, m), 3.93 (2H, q, J=7.2 Hz), 3.60 (3H, s), 2.75-2.50 (3H, m), 2.09 (3H, s), 2.08-2.00 (2H, m), 1.95-1.40 (8H, m), 1.27 (3H, t, J=7.2 Hz). MS (ES+) C24H34N6O2S requires: 470, found: 471 (1:1, 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, 1-Methyl-1H-imidazole-4-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chambers, Mark Stuart; Jones, Philip; Szekeres, Helen Jane; US2004/2504; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem