Category: 1849-01-0

Application of 1849-01-0, These common heterocyclic compound, 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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 69 1,3-Dihydro-1-methyl-3-(2-propynyl)-2H-benzimidazol-2-one potassium tert.-butoxide, 2.1 g (18.5 mmol). was added to a solution of 2.5 g (16.9 mmol) of 1,3-dihydro-1-methyl-2H-benzimidazol-2-one in 25 ml of dimethylformamide. After stirring under nitrogen for 15 minutes, 2.21 g (18.5 mmol) of propargyl bromide was added and the mixture was stirred at room temperature for 30 minutes. It was diluted with ice-water and the precipitate was filtered off washed with water and sucked dry. The crude product was passed over silica gel using 10% (v/v) of ethyl/acetate in methylene chloride for elution. Crystallization from ethyl acetate/hexane gave colorless crystals of 1,3-dihydro-1-methyl-3-(2-propynyl)-2H-benzimidazole-2-one with m.p. 110-112.

The synthetic route of 1849-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US4959361; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C8H8N2O, 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. 1849-01-0.

To a solution of 1,3-dihydro-1,N-methyl-2-oxobenzimidazole (3.185 g, 21.5 mmol) in DMF (60 mL) is added NaH (60% in mineral oil,1.03 g, 25.78 mmol) portionwise at 0 C. After stirring at 0 C for 30 min.2,4-dichloropyrimidine (3.20 g, 21.5 mmol) is added, and the mixture is allowed to stir at 15 C for 12 hrs. The resulting mixture is quenched with water (200 mL) and the mixture is extracted with EtOAc (100 mL x 3), and washed with water (100 mL x 4), dried with Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (petroleum ether: EtOAc =10:1), to give 2-chloro-4-(1,3-dihydro-3,N-methyl-2-oxobenzimimidazol-1-yl)pyrimidine.

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

Reference:
Patent; CS PHARMASCIENCES, INC.; SONG, Yuntao; BRDIGES, Alexander, James; (524 pag.)WO2017/120429; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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. 1849-01-0

Preparation of l-(3-iodopropyl)-3-methyl-l -benzor< |imidazol-2(3H)-one; [0176] A mixture of l-methyl-lH-benzo[i ]imidazol-2(3H)-one (2 g, 13.5 mmol, 1 equiv), 1- bromo-3-chloropropane (3.98 ml, 40.5 mmol, 3 equiv), and potassium carbonate (2.79 g, 20.25 mmol, 1.5 equiv) in NN-dimethylformamide was heated at 65C for 16 h. The reaction was cooled to ambient temperature and diluted with ethyl acetate. After being washed with water and brine, the organic layer was dried over MgS04, filtered, and concentrated in vacuo. The resulting residue was purified using the Biotage chromatography system (SNAP lOOg cartridge, Rf = 0.6, gradient - 10%- 50%) ethyl acetate/hexanes) to afford l-(3-chloropropyl)-3-methyl-lH-benzo[i ]imidazol-2(3H)-one as a clear oil (2.57 g, 85%); 'ffNMR (400 MHz, DMSO-i/6): delta 2.05-2.12 (m, 1H); 2.14-2.21 (m, 1H); 3.32 (s, 3H); 3.53 (t, 1H, J= 6.8 and 6.4 Hz); 3.66 (t, 1H, J= 6.4 Hz); 3.92-3.97 (m, 2H); 7.05- 7.09 (m, 2H); 7.12-7.16 (m, 1H); 7.17-7.21 (m, 1H); MS for CiiH13ClN20 m/z 226.07 (M+H)+. Statistics shows that 1849-01-0 is playing an increasingly important role. we look forward to future research findings about 1-Methyl-1H-benzo[d]imidazol-2(3H)-one. Reference:
Patent; ALTOS THERAPEUTICS, LLC; LUEHR, Gary, W.; SUNDARAM, Arathi; JAISHANKAR, Priyadarshini; PAYNE, Philip, W.; DRUZGALA, Pascal; WO2011/160084; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 1849-01-0 name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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. 1849-01-0

Example 7 Preparation of 1,3-dihydro-1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-2H-benzimidazol-2-one (Compound 159) A mixture of 3-[4-(chloromethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (i.e. the product of Example 1, Step B) (0.3 g, 1.1 mmol), 1,3-dihydro-1-methyl-2H-benzimidazol-2-one (0.17 g, 1.1 mmol) and cesium carbonate (0.56 g, 1.7 mmol) in N,N-dimethylformamide (2.5 ml) was stirred at room temperature for 12 h. The reaction mixture was partitioned between ethyl acetate (25 ml) and water (5 ml). The organic layer was separated and washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting material was purified by silica gel chromatography (eluting with a gradient of 0 to 50% ethyl acetate in hexanes) to provide the title compound, a compound of the present invention, as a solid (0.095 g). 1H NMR (CDCl3): delta 3.49 (s, 3H), 5.16 (s, 2H), 6.81-6.90 (m, 1H), 6.97-7.06 (m, 2H), 7.06-7.18 (m, 1H), 7.47 (d, 2H), 8.07 (d, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; FMC Corporation; PASTERIS, Robert James; CHITTABOINA, Srinivas; MCMAHON, Travis Chandler; KAMIREDDY, Balreddy; REDDY, Ravisekhara Pochimireddy; (121 pag.)US2020/148672; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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 1849-01-0, 1849-01-0

To a stirred solution of l-methyl-2,3-dihydro-lH-l,3-benzodiazol-2-one (217 mg, 1.46 mmol) in DMF (2 mL) was added NaH (64.5 mg, 1.61 mmol, 60% w/w dispersed into mineral oil) at 0 C under nitrogen atmosphere. The reaction mixture was stirred for 20 min at 0 C. To the above mixture was added dropwise a solution of 3-bromopiperidine-2,6-dione(140.6 mg, 0.73 mmol) in DMF (0.5 mL) at 0 C. The resulting mixture was stirred for additional 3 hours at room temperature. The resulting mixture was quenched with AcOH (0.5 mL) and was concentrated under reduced pressure. The crude product was purified by prep-HPLC with the following conditions: Column: XBridge Shield RP18 EVO Column, 5 um, 19 x 150 mm; Mobile Phase A: water (plus 0.05% FA), Mobile Phase B: ACN; Flow rate: 20 mL/min; Gradient: 10% B to 35% B in 7 min; Detector: UV 220 nm; Rt: 6.30 min. Desired fractions were collected and concentrated under reduced pressure. The residue was lyophilized to afford 3-(3-methyl-2-oxo-2,3-dihydro-lH- l,3-benzodiazol-l-yl)piperidine-2,6-dione, 1-2, as a white solid (30.4 mg, 21%): NMR (400 MHz, OMSO-d6) delta 11.03 (br s, 1H), 7.13 – 6.97 (m, 4H), 5.30 (dd, J= 12.7, 5.4 Hz, 1H), 3.35 (s, 3H), 2.90 – 2.78 (m, 1H), 2.73 – 2.49 (m, 2H), 2.03 – 1.90 (m, 1H); LC/MS (ESI, m/z): [(M + 1)]+ = 260.2.

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-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; MAINOLFI, Nello; JI, Nan; ZHANG, Yi; WEISS, Matthew M.; (223 pag.)WO2019/60693; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 1849-01-0 name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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. 1849-01-0

Step A: 5-(3-Methyl-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-thiazolidine-2,4-dione (I-51). To a solution of 1-methyl-1,3-dihydro-benzoimidazol-2-one (300 mg, 1.13 mmol) in DMF (4.0 mL) was added NaH (60% in mineral oil, 101.7 mg, 3.39 mmol) at 0 oC under nitrogen. The reaction mixture was stirred at 0 oC under N2 for 30 minutes. Then 5-bromo-thiazolidine-2,4- dione (230 mg, 1.13 mmol) in DMF (1 mL) was added slowly. After stirring at r.t. for 10 minutes, the reaction was quenched with water (30 mL) and extracted with EtOAc (50 mL x 3). The combined organic layer was washed with brine and dried over Na2SO4. The mixture was filtered and the filtrate solvent was removed under reduced pressure. The residue was purified via silica gel column chromatography (Petroleum ether/EtOAc) to give the title compound (22 mg, 7.4% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm: 12.7 (s, 1H), 7.76-7.13 (m, 5H), 3.34 (s, 3H). LC-MS: Calculated exact mass = 263.0; Found [M+H]+ = 263.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; MAINOLFI, Nello; JI, Nan; KLUGE, Arthur F.; (282 pag.)WO2019/140387; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1849-01-0, The chemical industry reduces the impact on the environment during synthesis 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, I believe this compound will play a more active role in future production and life.

General procedure: One equivalent of appropriate heterocyclic derivative was dissolved in DMF. Three equivalents of potassium carbonate and 1.2 equivalent of the appropriate 3-chloropropan-1-amine derivative were added. The resulting mixture was heated at 70C until disappearance of the starting material. The reaction was monitored by TLC. After 24-96 h, the solvent was removed under reduced pressure, and water added to the residue. The crude product was extracted with dichloromethane. The combined organic fractions were washed with water and dried over magnesium sulphate. Purification by thick layer chromatography or column chromatography was performed.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-benzo[d]imidazol-2(3H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Donnier-Marechal, Marion; Carato, Pascal; Le Broc, Delphine; Furman, Christophe; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 575 – 582;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem