Tag: M.W=100-200

Reference of 615-16-7, These common heterocyclic compound, 615-16-7, name is 2-Hydroxybenzimidazole, 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 benzimidazole-2-one (Aldrich, 1.1 g, 7.5 mmol) in DMF (20 ml) was added 3,6-dichlorobenzoisoxazole (1.5 g, 7.5 mmol) and Cs2CO3 (4.8 g, 15 mmol). The suspension was heated to 15O0C in an oil bath and stirred overnight. The mixture was then cooled to room temperature, diluted with water (30 ml) and stirred in a ice bath for 2 hours. The mixture was then filtered. The solid was washed with water and dried under high vacuum to obtain 2.0 g (93%) of a yellow solid as l-(6-chlorobenzisoxazol-3-yl)benzimidazole-2-one. To a solution of the above product (1.0 g, 3.5 mmol) in DMF (15 ml) was added NaOMe solution in methanol (30% wt/wt, 10 ml). The mixture was heated to 8O0C under vacuum to remove residual methanol and then stirred at 11O0C under nitrogen overnight. The mixture was then cooled to room temperature, diluted with water (50 ml), adjusted to pH 6 with 10% aqueous HCl. The resulting suspension was stirred in an ice bath for 2 hours and filtered. The solid was washed with water and dried in an oven (900C) for 2 hours and then under high vacuum at room temperature for 3 hours to obtain a slightly yellow solid. LC-MS m/e: (M+ 1) = 282

Statistics shows that 2-Hydroxybenzimidazole is playing an increasingly important role. we look forward to future research findings about 615-16-7.

Reference:
Patent; MERCK & CO., INC.; WO2006/22954; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 78581-99-4, 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. 78581-99-4, name is 5,6-Difluorobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of (lR,3S,5S,6r)-6-(((S)-l,l-dimethylethylsulfinamido)methyl) bicyclo[3.1.0]hexan-3-yl methanesulfonate (1.42 g, 4.59 mmol) in THF (15.30 mL) was added cesium carbonate (4.49 g, 13.77 mmol) and 5,6-difluoro-lH-benzo[d]imidazole (0.849 g, 5.51 mmol) and the resulting mixture was stirred at 85C for 16 h. The reaction was cooled to RT, concentrated, diluted with water and extracted twice with EtOAc. The organics were washed with brine, combined, dried over MgS04, concentrated and purified by flash chromatography (5 to 40% of 80:20:2 EA:EtOH:NH40H in hexanes) to give (S)-N- (((lR,3R,5S,6r)-3-(5,6-difluoro-lH-benzo[d]imidazol-l-yl)bicyclo[3.1.0]hexan-6-yl)methyl)- 2-methylpropane-2-sulfinamide (1.03 g, 2.80 mmol, 61.1 % yield) as a white solid. MS (ES+) C18H23F2N3OS requires: 367, found: 368 [M+H]+.

The synthetic route of 5,6-Difluorobenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TESARO, INC.; LEWIS, Richard, T.; HAMILTON, Matthew; JONES, Philip; PETROCCHI, Alessia; REYNA, Naphtali; CROSS, Jason; HAN, Michele; SOTH, Michael; MCAFOOS, Timothy; TREMBLAY, Martin; (356 pag.)WO2018/136437; (2018); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 583-39-1, 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 583-39-1 as follows.

Sodium hydroxide (1.60 g, 40 mmol) was dissolved in 2-PrOH (70 ml), benzimidazole-2-thione 1 (6.00 g, 40 mmol) was added followed by portionwise addition of chloroacetamide (3.75 g, 40 mmol). The reaction mixture was refluxed for 3 h, cooled, the precipitate was filtered off, washed with water, and dried. Yield 6.75 g (81%), colorless crystals

According to the analysis of related databases, 583-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bespalov; Gorchakova; Ivanov; Kuznetsov; Kuznetsova; Pankova; Prokopenko; Avdontceva; Chemistry of Heterocyclic Compounds; vol. 50; 11; (2015); p. 1547 – 1558;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 75370-65-9, 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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Commercially available (6-chloropyridin-3-yl)methanamine (1 g, 7 mmol) was dissolved in 40 ml of AcOEt and at OC triphosgene (1.93 g,7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 10ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10ml) of compound la (1 g, 6.7 mmol) and the mixture was warmed at 80C for8 hours. (TLC AcOEt 9.5 / MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (80 ml) and washed with water (1 X 40 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 450 mg of a pale yellow solid. Yield = 21% ‘HNMR (DMSO, 200 MHz) delta 4.32 (2H, d, J = 5.8 Hz), 6.62 (1H, d, J = 7.2 Hz), 6.85 (3H, m), 7.48 (1H, d, J = 8.4 Hz), 7.81 (1H, dd, J = 8.2 Hz, J’ = 2.4 Hz), 8.33 (2H, m), 10.02 (1H, bs), 10.60 (1H, bs); [M+1] 317.8 (C14H12ClN5O2 requires 317.73).

The synthetic route of 4-Amino-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); 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

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

Related Products of 39070-14-9,Some common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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 a solution of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (6) (1 eq.) in freshly distilled anhydrous THF (10?mL for 3?mmol of alcohol 6) was added dropwise lithium bis(trimethylsilyl)amide (1?M in THF, 1.1 eq.) at -78?C under an inert atmosphere. The reaction mixture was stirred around 5?min?at -78?C, and a solution of bis(2-chloroethyl)phosphoramidic dichloride (8) (1.1 eq.) in THF (3.3?mmol in 10?mL), previously cooled at -78?C, was added all at once at the same temperature (T0). The reaction mixture was stirred for 15-80?min, before the addition of a solution of the appropriate amine 18-22 (2-2.2 eq.) in THF (3?mL for 5?mmol of amine) and stirring was maintained at -78?C for 5?min to 75?min. These reaction times were determined by 31P NMR monitoring for each compound. The reaction was stopped by addition of water (20?mL for 3?mmol of alcohol 6), concentrated in vacuum and then extracted with EtOAc (3?*?50?mL for 3?mmol of alcohol 6). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using an eluent gradient (EtOAc/EtOH with TEA or NH4OH) to afford compounds 23-27 as yellow to orange oils.

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-2-nitro-1H-imidazol-5-yl)methanol, its application will become more common.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 52099-72-6,Some common heterocyclic compound, 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C10H10N2O, 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.

Compound III-1 (1.74 g, 10 mmol) represented by the following structural formulaPotassium carbonate (2.74 g), 1,4-dibromopropane (6.07 g, 30 mmol) was added to a solution of (20 ml) in DMF for 3 hours,Stir at 60 C. Water was added to the reaction solution, and extracted with ethyl acetate.The organic layer was washed with brine and dried over Na 2 SO 4. Filtration,After evaporation of the solvent, the residue is subjected to silica gel column chromatographyPurification by (AcOEt / n-hexane 1: 4) gave compound III-2 (1.961 g, 66%) as a colorless oil.

The synthetic route of 52099-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tokyo Medical and Dental University; Hata, Yutaka; Kagechika, Hiroyuki; Ito, Shigeru; Tsuemoto, Nozomi; kodaka, Manami; Dilihumaer, Ainiwaer; (24 pag.)JP2019/89720; (2019); A;,
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. 3304-70-9, name is Dimethyl 4,5-imidazoledicarboxylate, A new synthetic method of this compound is introduced below., Formula: C7H8N2O4

lH-Imidazole-4,5-dicarboxylic acid dimethyl ester (592 mg, 3.21 mmol) is combined with hydrazine (600 mg, 18.8 mmol) and MeOH (10 mL). The reaction mixture is heated to 115C for 30 min. Cool and filter off the resulting precipitate. Wash with additional water. Combine the precipitate with hydrazine (1.38 mL) and reflux for 4 h. Pour the reaction mixture into ice water and adjust the to pH 2 with HCl (12 N). The new precipitate is isolated by filtration to afford the title product (293 mg, 60%) 1H NMR (400 MHz, DMSO-^6) delta 11.41 (br. s., 1.47 H), 8.27 (s, 1 H), 3.37 (br. s., 6.2 2H).

The synthetic route of 3304-70-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1615-14-1, These common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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.

Synthesis of 10-(2-(1H-Imidazol-1-yl)ethyl) 2-benzyl (25,4a5,6a5,6bR,8a5, 105, 12a5, l2bR, l4bR)-2,4a,6a,6b,9,9, 12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9, 10, 11, 12, 12a, 1 2b, 13,1 4b-icosahydropicene-2, 1 0-dicarboxylate (7-1). Into a 25 -mL round-bottom flask, wasplaced 1-7 (137 mg, 0.23 mmol, 1.00 equiv.), DCM (10 mL), 2-(1H-imidazol-1-yl)ethan-1-ol (51 mg, 0.45 mmol, 2.00 equiv.), DMAP (3 mg, 0.02 mmol, 0.10 equiv.), TEA (0.047 mL, 1.50 equiv.). The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with DCMIMeOH(20:1). This resulted in 140mg (91%) of 7-1 as a white solid.

The synthetic route of 1615-14-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; LUEHR, Gary; DRAGOLI, Dean; LEADBETTER, Michael; CHEN, Tao; LEWIS, Jason; (181 pag.)WO2019/60051; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem