Tag: M.W=100-200

1003-21-0,Some common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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 5-bromo-1-methyl-1H-imidazole (3.22 g, 19.98 mmol) in DCM (15 mL) was added ethyl magnesium bromide (6.66 mL, 19.98 mmol, 3.0 M in diethyl ether) dropwise over a 10 minute period. The resulting orange-red solution was stirred at room temperature for 15 minutes, cooled in an ice bath to 0 C. and N-methoxy-N-methyl-4-nitrobenzamide (3.5 g, 16.65 mmol, Intermediate 7: step a) dissolved in DCM (10 mL) was added dropwise. The ice bath was removed and the solid suspension stirred at room temperature for 48 hours. Water was added followed by 6 M aqueous HCl to a neutral pH (pH=6-7). The aqueous mixture was extracted with DCM, dried over Na2SO4, filtered and concentrated. Et2O was added and the mixture sonicated. The precipitate was collected by filtration and dried to provide the title compound as a tan solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methyl-1H-imidazole, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; (53 pag.)US2017/258782; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding some certain compound to certain chemical reactions, such as: 312-73-2, name is 2-(Trifluoromethyl)-1H-benzo[d]imidazole, 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 312-73-2. 312-73-2

General procedure: A solution of this chloromethyl ester (1.8 mmol) in N,N-dimethylformamide (4 ml) was treated with the 2-substituted benzimidazoles (1.8 mmol) and cesium carbonate (2.8 mmol). The mixture was stirred for 3 h at r.t. and partitioned with water and ethyl acetate (20 ml). The aqueous layer was further extracted with ethyl acetate (20 ml) and the combined organic layers washed with brine (20 ml), dried (sodium sulfate), filtered and concentrated. Flash chromatography with ethyl acetate provided the desired product as colored oil.

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 2-(Trifluoromethyl)-1H-benzo[d]imidazole.

Reference:
Article; Sengupta, Prabal; Puri, Chetan S.; Chokshi, Hemant A.; Sheth, Chetana K.; Midha, Ajay S.; Chitturi, Trinadha Rao; Thennati, Rajamannar; Murumkar, Prashant R.; Yadav, Mange Ram; European Journal of Medicinal Chemistry; vol. 46; 11; (2011); p. 5549 – 5555;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

51605-32-4, A common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, molecular formula is C7H10N2O2, 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.

Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate (EV-AT8648-001)? Step 1 To a stirred solution of ethyl 4-methyl-1H-imidazole-5-carboxylate (CAS 51605-32- 4, 500 mg, 3.24 mmol) in acetonitrile (10 ml) and chloroform (10 ml) was added N- bromosuccinimide (577 mg, 3.24 mmol) and the reaction stirred under a nitrogen atmosphere at room temperature for 18h. The reaction mixture was concentrated and the residue was purified by flash column chromatography (10-100percent ethyl acetate/heptane) to afford 560 mg (73percent) of ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate (EV-AT8648-001) as an off-white solid. LCMS (method D): retention time 0.87 min, M/z = 233/235 (M + 1).

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PADLOCK THERAPEUTICS, INC.; DEVRAJ, Rajesh; KUMARAVEL, Gnanasambandam; ATTON, Holly; BEAUMONT, Edward; GADOULEAU, Elise; GLEAVE, Laura; KERRY, Philip Stephen; LECCI, Cristina; MENICONI, Mirco; MONCK, Nat; PALFREY, Jordan; PAPADOPOULOS, Kostas; TYE, Heather; WOODS, Philip A.; (158 pag.)WO2017/147102; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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. 41716-18-1

Preparation of Compound 69aAt 0¡ã C., a suspension of 1-methyl-1H-imidazole-4-carboxylic acid (100.9 mg, 0.8 mmol) in CH2Cl2 (8 mL) was added oxalylchloride (305 mg, 0.21 mL, 2.4 mmol) followed by addition of 1 drop of DMF. The mixture was stirred for 2 days at 25¡ã C. All solvent was removed in vacuo to give a crude 69a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41716-18-1, its application will become more common.

Reference:
Patent; Pfizer Inc.; US2009/318440; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1546-79-8, 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 1546-79-8 as follows.

5-[4-Fluoro-5-(4-bromophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridinesulfonamide (Step 2) To a solution of 1-(4-bromophenyl)-2-fluoro-1-ethanone (3.54 g, 16.3 mmol) in tetrahydrofuran (50 ml) was added dropwise 1M lithium hexamethyldisilazide tetrahydrofuran solution (19.6 ml, 19.6 mmol) at -78 C. After stirring for 45 min., N-trifluoroacetylimidazole (2.3 ml, 19.6 mmol) was added. The resulting mixture was allowed to warm up to room temperature and stirred for 1.5 hr. The mixture was acidified with 2M hydrochloric acid and extracted with diethyl ether (300 ml). The separated organic layer was washed with water (100 ml*3) and dried over magnesium sulfate. The solution was evaporated to give 5.2 g of 1-(4-bromophenyl)-2,4,4,4-tetrafluoro-1,3-butanedione as a brown oil.

According to the analysis of related databases, 1546-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; US2003/144280; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1615-14-1, Adding a certain compound to certain chemical reactions, such as: 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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 1615-14-1.

A 50-mL three-necked, round-bottomed flask, equipped with thermometer, nitrogen inlet, addition funnel, magnetic stirrer and reflux condenser was flame dried and flushed with nitrogen. The flask was charged with 25 ml_ of anhydrous dichloromethane. Freshly distilled 1-ethanol imidazole (1, 0.01 mol) was added into the flask. The flask was chilled with ice-water bath and benzyl chloride (0.011 mol) in 15 ml_ of anhydrous dichloromethane was added cautiously into the flask with continous stirring over 20 minutes. The solution was heated under reflux for 5 hours and then allowed to cool to room temperature. The dichloromethane solvent was distilled under to give 92% of 3-benzyl-1-ethanol imidazolium chloride 5.

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, 2-(1H-Imidazol-1-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MIMOS BERHAD; AHMAD, Mohd Rais; WO2010/33014; (2010); A2;,
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

496-46-8, Adding some certain compound to certain chemical reactions, such as: 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 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 496-46-8.

14.2 g (100 mmol) of glycoluril,16.0 g (400 mmol) of sodium hydroxide and 140 mL of dimethylsulfoxide were mixed,After heating and stirring at 40 C. for 1 hour, And 34.4 g (400 mmol) of allyl chloride were added dropwise at the same temperature over 20 minutes, and the mixture was heated and stirred at 40 C. for 2 hours to complete the reaction.The resulting reaction mixture was evaporated to dryness under reduced pressure, and the obtained dry solid was separated and extracted with 400 mL of ethyl acetate and 400 mL of water, and the ethyl acetate layer was washed with 100 mL of water, then with 100 mL of saturated brine, Dried over sodium sulfate, and ethyl acetate was distilled off under reduced pressure to obtain 27.4 g of 1,3,4,6-tetraallyl glycoluril as a colorless oil, yield 90%.

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 496-46-8.

Reference:
Patent; Shikoku Chemicals Co., Ltd.; Takeda, Takuma; Kashihara, Takashi; Kumano, Noboru; Mizobe, Noboru; (59 pag.)JP2015/59101; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15965-54-5, 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 15965-54-5 as follows.

General procedure: A mixture of 10 (5 mM), 11 (5 mM) in DMF (20 mL) containing K2CO3 (2 mM) and TBAB (2 mM) was stirred at RT for a period of 3-5 h. The reaction was monitored by TLC analysis. After the completion of reaction, the mixture was poured into ice-cold water (30 mL). The separated solid was filtered, washed with water (2 9 10 mL) and dried. The crude product was recrystallized from a suitable solvent to yield pure 9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 15965-54-5, and friends who are interested can also refer to it.

Reference:
Article; Srikrishna, Devulapally; Dubey, Pramod Kumar; Research on Chemical Intermediates; vol. 44; 7; (2018); p. 4455 – 4468;,
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