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., Recommanded Product: 137049-00-4

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

137049-00-4, Name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 137049-00-4, 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.

To a solution of intermediate 2.103 (20. mg, 0.078 mmol) and triethylamine (30 muL, 0.2 mmol) in dichloromethane (0.5 mL) at 0 C 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 DMSO (1 mL), filtered through Celite and purified via mass-directed isolation using ultra-performance liquid chromatography (18 mg, 57% yield).1H NMR (500 MHz, (0494) Acetonitrile-d3) d 8.61 (s, 1H), 7.73 (s, 1H), 7.69 (dd, J = 11.8, 2.4 Hz, 1H), 7.57 (d, J = 1.4 Hz, 1H), 7.37 (t, J = 8.6 Hz, 1H), 7.26- 7.18 (m, 1H), 3.85- 3.77 (m, 1H), 3.73 (s, 3H), 3.64 (d, J = 12.0 Hz, 1H), 2.67 (t, J = 11.2 Hz, 1H), 2.62- 2.47 (m, 2H), 1.85- 1.76 (m, 1H), 1.59 (qt, J = 12.5, 4.0 Hz, 1H), 1.53- 1.41 (m, 1H); AMM 423.0678 (ESI) m/z [calc for (0495) C16H18ClFN4O3SNa (M+Na)+ 423.0670].

Statistics shows that 1-Methyl-1H-imidazole-4-sulfonyl chloride is playing an increasingly important role. we look forward to future research findings about 137049-00-4.

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

Electric Literature 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

Reference of 137049-00-4, 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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of N-[4-methyl-5-(lH-pyrazol-4-yl)-l,3-thiazol-2-yl]acetamide, compound (3) (44 mg; 0.2 mmol; 1 eq.), 1 -methyl- lH-imidazole-4-sulfonyl chloride (36 mg; 0.2 mmol; 1 eq.) and N,N-diisopropylethylamine (0.1 ml; 0.6 mmol; 3 eq.) in DCM (2 ml) was stirred overnight at RT. The reaction mixture was diluted with DCM and washed with water and brine. Organic phase was dried over MgSO4, filtered and evaporated. The resulting crude product was purified by flash chromatography (CHCl3ZMeOH gradient from 100:1 to 50: 50), affording compound (8) as light yellow solid (35 mg; 47.5 %). 1U NMR (DMSO-d6) delta 2.12 (s, 3H), 2.32 (s, 3H), 3.72 (s, 3H), 7.86 (m, IH), 8.06 (s, IH), 8.30 (m, IH), 8.47 (s, IH), 12.11 (br s, IH). M”(ESI): 365.25; M+(ESI): 367.23. HPLC, Rt: 2.31 min (purity: 98.4%).

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; LABORATOIRES SERONO S.A.; WO2007/82956; (2007); A1;,
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., HPLC 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

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., HPLC of Formula: C4H5ClN2O2S

To a precooled (0 C) solution of intermediate 2.66 (18 mg, 0.074 mmol) and triethylamine (30 muL, 0.2 mmol) in dichloromethane (0.5 mL) was added 1-methyl-1H- imidazole-4-sulfonyl chloride (20. mg, 0.11 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 18 h, then diluted with wet DMSO (1 mL), filtered through Celite and purified via mass-directed isolation using ultra-performance liquid chromatography (6.3 mg, 22% yield).1H NMR (500 MHz, Acetonitrile-d3) d 8.56 (s, 1H), 7.69 (s, 1H), 7.66 (dd, J = 11.8, 2.4 Hz, 1H), 7.59 (d, J = 1.4 Hz, 1H), 7.37 (t, J = 8.6 Hz, 1H), 7.21 (dd, J = 8.7, 2.1 Hz, 1H), 3.72 (s, 3H), 3.63 (dd, J = 10.4, 7.9 Hz, 1H), 3.50- 3.40 (m, 2H), 3.40- 3.32 (m, 1H), 3.00 (p, J = 7.6 Hz, 1H), 2.14- 1.96 (m, 2H); AMM 409.0521 (ESI) m/z [calc for C15H16ClFN4O3SNa (M+Na)+ 409.0513].

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; 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

Application 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.

To methyl 4-{2-[2-(2-aminoethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]ethoxy}benzoate (Step 6, Example 1) (1.0 equiv) and Et3N (3.0 equiv) or pyridine (3.0 equiv) in CH2Cl2 (0.05 M) was added 1-methylimidazole-4-sulfonyl chloride (1.2 equiv). The reaction was monitored by TLC (10% MeOH-CH2Cl2) and was heated if necessary. After 30 min the mixture was poured into saturated sodium bicarbonate and extracted with CH2Cl2. The combined organic phase was washed with brine, dried over sodium sulfate and purified by column chromatography to afford 92% of the desired product.

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; Wyeth; US2008/9485; (2008); 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.

To a precooled (0 C) solution of intermediate 2.55 (20. mg, 0.078 mmol) in dichloromethane (0.5 mL) was added triethylamine (30 muL, 0.2 mmol) and 1-methyl-1H- imidazole-4-sulfonyl chloride (21 mg, 0.12 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 15 h, then diluted with wet DMSO (0.5 mL), filtered through Celite and purified via mass-directed isolation using ultra-performance liquid chromatography (14 mg, 45% yield).1H NMR (500 MHz, Acetonitrile-d3) d 7.63 (d, J = 1.4 Hz, 1H), 7.56 (d, J = 1.4 Hz, 1H), 7.51 (t, J = 8.6 Hz, 1H), 7.11 (dd, J = 9.9, 2.6 Hz, 1H), 7.01- 6.95 (m, 1H), 3.75- 3.72 (m, 1H), 3.71 (s, 3H), 3.40 (dd, J = 12.3, 5.1 Hz, 1H), 3.10 (dd, J = 12.1, 9.1 Hz, 1H), 2.92 (tt, J = 9.0, 4.0 Hz, 1H), 2.81 (ddd, J = 12.9, 9.6, 3.4 Hz, 1H), 2.05- 1.97 (m, 1H), 1.87- 1.78 (m, 1H), 1.70- 1.56 (m, 2H); AMM 402.0697 (ESI) m/z [calc for C16H18ClFN3O4S (M+H)+ 402.0691].

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.

Sodium hydride (33mg, 2eq) Soluble in 5mL anhydrous tetrahydrofuran, Compound Ib (190 mg, 1 eq) was added in portions with stirring. After stirring at room temperature for 30 minutes, Methylpyrazolesulfonyl chloride (157 mg, 1.3 eq) Dropped into the reaction solution, Stir at room temperature for 6 h, After the reaction is complete, Concentrate to tetrahydrofuran, Add 100mL of water, Adjust PH to nearly 7, Extracted with ethyl acetate three times, The organic layer was dried over anhydrous sodium sulfate and concentrated. The title compound 101 (219 mg, yield: 76%) was obtained.

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; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Shen Jingkang; Ding Jian; Geng Meiyu; Xiong Bing; Ai Jing; Ma Yuchi; Dai Yang; (77 pag.)CN108570052; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products 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.

Example 15(6-{[4-(1-Butylcyclopropyl)benzyl](1-methyl-1H-imidazol-4-ylsulfonyl)aminomethyl}pyridin-2-ylamino)acetic acid (Exemplary compound No. 1138)15-(a): tert-Butyl [tert-butoxycarbonyl(6-{[4-(1-butylcyclopropyl)benzyl](1-methyl-1H-imidazol-4-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]acetateTo 6 ml of a methylene chloride solution containing 307 mg (0.586 mmol) of tert-butyl [tert-butoxycarbonyl(6-{[4-(1-butylcyclopropyl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate obtained in Reference example 13 were added uncer ice-cooling 163 mul (1.17 mmol) of triethylamine and 127 mg (0.703 mmol) of 1-methyl-1H-imidazol-4-ylsulfonyl chloride, and the mixture was stirred at the same temperature for 2.5 hours and at room temperature for 6 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was applied to silica gel column chromatography (eluent; n-hexane:ethyl acetate=3:7?1:3 (V/V)), and the fractions containing the objective material were concentrated under reduced pressure to obtain 293 mg of the title compound as colorless oily product. (Yield: 75%)Mass Spectrum (CI, m/z): 668 (M++1).1H-NMR Spectrum (CDCl3, delta ppm): 7.65 (d, J=8.2 Hz, 1H), 7.46 (dd, J=8.2, 7.4 Hz, 1H), 7.38 (d, J=1.2 Hz, 1H), 7.18 (d, J=1.2 Hz, 1H), 7.15 (s, 4H), 6.96 (d, J=7.4 Hz, 1H), 4.58 (s, 2H), 4.50 (s, 2H), 4.38 (s, 2H), 3.67 (s, 3H), 1.55-1.47 (m, 2H), 1.52 (s, 9H), 1.43 (s, 9H), 1.26-1.15 (m, 4H), 0.83 (t, J=6.8 Hz, 3H), 0.74-0.68 (m, 2H), 0.66-0.59 (m, 2H).

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

Reference:
Patent; UBE INDUSTRIES, LTD.; US2012/259123; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem