Imidazoles-derivatives

Electric Literature of 583-39-1, The chemical industry reduces the impact on the environment during synthesis 583-39-1, name is 2-Mercaptobenzimidazole, I believe this compound will play a more active role in future production and life.

Thione 2b (150 mg, 1.0 mmol) was added to a stirred solution of MeOK (77 mg, 1.1 mmol) in anhydrous MeOH (2 ml). The obtained solution was added to ketone 1d (311 mg, 1.0 mmol) in anhydrous MeOH (5 ml). The reaction mixture was stirred for 24 h, the precipitate that formed was filtered off, washed with cold 70% EtOH, and air-dried. Yield 245 mg (53%), light yellow crystals, mp 153-154C (Me2CO-H2O). IR spectrum, nu, cm-1: 3139, 3115, 3048, 1597, 1585, 1539,1517, 1496, 1477, 1440, 1406, 1007, 985, 965, 923, 905,880, 847, 827, 816, 794, 750, 717. 1H NMR spectrum, delta,ppm (J, Hz): 6.44 (1, d, J = 3.2, H Fur); 6.47 (1H, s,SCH); 6.90 (1, d, J = 3.2, H Fur); 7.13-7.19 (2, m,H Ar); 7.33 (1H, t, J = 7.2, H Ar); 7.38-7.43 (5, m,H Ar); 7.53-7.58 (3, m, H Ar); 7.61 (2, d, J = 7.8,H Ar); 12.76 (1H, s, NH). 13C NMR spectrum, delta, ppm:48.5; 107.9; 111.2 (2C); 118.3; 121.9; 122.6; 125.4 (2C);128.6 (3C); 129.2; 129.3 (2C); 129.4 (2C); 132.4; 135.7;138.5; 144.1; 148.0; 152.4; 153.5. Found, %: 62.38; 4.00. C24H17BrN2OS. Calculated, %: 62.48; 3.71.

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-Mercaptobenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Golovanov, Alexander A.; Bekin, Vadim V.; Zlotskii, Simon S.; Kunavin, Yurii A.; Vologzhanina, Anna V.; Gusev, Dmitry M.; Bunev, Alexander S.; Chemistry of Heterocyclic Compounds; vol. 51; 10; (2015); p. 929 – 932; Khim. Geterotsikl. Soedin.; vol. 51; 10; (2015); p. 929 – 932,4;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 17289-26-8, A common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

[00215] Examples 22 and 33 were synthesized via parallel synthesis according to the following method. To each microwave vial containing an aldehyde (0.08 mmol) corresponding to the R3 group contained in Examples 13-36 was added MeOH (0.65 mL) and CH3NH2 (2.0 M in THF; 0.04 mL, 0.08 mmol). The reaction mixtures were heated to 60 C for 10 min using microwave irradiation, then cooled to rt. To each reaction mixture was added a 0.24 M solution of Intermediate 5 in MeOH (0.22 mL, 0.05 mmol). The resulting reaction mixtures were heated to 100 C for 20 min using microwave irradiation. After cooling to rt, they were diluted with MeOH (0.25 mL). Examples 22 and 33 were purified from their corresponding solutions by RP preparative HPLC using Method H. HPLC/MS data for each compound was collected using Method E, and the molecular masses of the compounds were determined by MS (ES) by the formula m/z. Both the retention time and MS data are listed in Table 2.

The synthetic route of 17289-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ABELL, Lynn; ADAM, Leonard; CAVALLARO, Cullen L.; FINLAY, Heather; FRIENDS, Todd J.; HANGELAND, Jon J.; JIANG, Ji; LAWRENCE, R. Michael; LLOYD, John; PI, Zulan; TORA, George O.; QIAO, Jennifer X.; HU, Carol Hui; WANG, Tammy C.; WO2013/48982; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1546-79-8, 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. 1546-79-8 name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, 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.

I -(‘rrifliioroacetyl)iniida ole (37.7 p.L, 331 mueta,iotaomicronIota, 6.00 equiv) was added dropwise to a solution of I2-p ~mutilm 94 (17.7 mg. 55.2 mutauetaomicron, 1 equiv) in ethyl acetate (1.0 mL) at -78 C. The resulting mature was stirred for 50 mm a -78 C. The product mixture was diluted with aqueous hydrochloric acid solution (1 , 200 pL) and then was wai’med to 22 C over 1 h. The warmed product .mixture was diluted with aqueous hydrochloric acid solution (.1 M, 1. mL), The diluted product mixture was extracted with ethyl acetate (3 x 5 mL). The organic layers were combined and the combined organic layers were dried over sodiam sulfate. The dried solution was filtered and the. filtrate was concentrated. The residue obtained was purified by preparative thiii-layered chromatography (elutiog with 40% ether-pentaue) to provide the ester S16 as a white solid (15.0 mg, 65%). Rf~ 0.65 (40% ether-pentane, PAA stains purple) H NMR (500 MHz, CDCU) 5.62 (dd, ./= 17.4, 10.8 Hz, 1 H), 5.12-4.98 (m, 3H), 4,39-4.33 (m, IH), 2.53 (p, J – 7.2 Hz, 1H), 2.38-2.03 (m, 4H), 1.82-L66 (m, 3H), 1.60-1.40 (m, 3H), 1.38 (s, 3H 1 -33 (s, 3H), 1.29-1.13 (m, 2H), 0.99 (d, J = 7.1 Hz, 3H 0.83 (d, J = 7.1 Hz, Ml } 5SF NMR (470 MBzs CD?)?-75.09 (s, 3F). ,3C NMR (151 MHz, CDC ) 216.8, 156.8 (q, / – 42.0 Hz), 145,0, 1 14.8 (q, J~ 286.1 Hz), 1 14.0, 80.1, 66.4, 59.2, 46.0, 45.2, 43.8, 42.7, 36.9, 34.9, 34.5, 30.4, 27.3, 25.3, 183, 15.0, 13,5, 1 1 ,6. HRMS-ESI (m/z): calculated for [C22- FjOjN ]”*’ 439.2067, found 439.2046.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; YALE UNIVERSITY; HERZON, Seth; MURPHY, Stephen, K.; ZENG, Mingshuo; (194 pag.)WO2018/144717; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 930-62-1, The chemical industry reduces the impact on the environment during synthesis 930-62-1, name is 2,4-Dimethylimidazole, I believe this compound will play a more active role in future production and life.

Intermediate 18: step a 1-(2,4-Dimethyl-imidazol-1-yl)-ethanone The title compound was prepared according to the procedure described in J. Org. Chem. 1983, 48, 897: To a solution of 2,4-dimethylimidazole (4.00 g, 41.6 mmol) in toluene/chloroform (1/1, v/v, 50 mL) at room temperature was added acetyl chloride (1.48 mL, 20.8 mmol) dropwise over several minutes. The reaction was stirred at room temperature for 2 hours and filtered. The filtrate was evaporated, ethyl acetate was added and the solution was filtered again. The filtrate was evaporated to give the title compound.

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, 2,4-Dimethylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JACKSON, Paul Francis; Manthey, Carl; Rhodes, Kenneth; Scannevin, Robert; Leonard, Kristi Anne; Barbay, Joseph Kent; Todd, Matthew; Springer, Barry A.; US2012/302573; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 288-32-4,Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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: A mixture of imidazole (1 mmol), phenylboronic acid (2 mmol), K2CO3 (2 mmol), Cu(CH3COO)2H2O (1 mol %, 1.99 mg) and L1 (1 mol %, 5.7 mg) in ethanol (5 mL) was stirred at room temperature in a 50 mL oven dried round bottomed flask. After the completion of the reaction (as monitored by TLC), conventional workup of the reaction mixture was done with ethyl acetate (3 ¡Á 15 mL) and water (10 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered and the solvent was evaporated in a rotary evaporator under reduced pressure to get the crude product. The crude product was purified by column chromatography on silica gel (DCM: Methanol = 9:1) to afford the pure product.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baruah, Jayantajit; Gogoi, Kongkona; Dewan, Anindita; Borah, Geetika; Bora, Utpal; Bulletin of the Korean Chemical Society; vol. 38; 10; (2017); p. 1203 – 1208;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 40197-20-4, name is 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid, 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. name: 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid

[0055] N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride (1.2 g) was added to a mixture of 5-bromo-1H-benzimidazol-2-carboxylic acid (1.0 g), 1-[4-(trifluoromethyl)benzyl]piperazine (1.0 g), 1H-benzotriazol-1-ol (840 mg),and N,N-dimethylformamide (10 ml: hereinafter, abbreviated as DMF), followed by stirring at room temperature overnight.A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, followed by stirring atroom temperature for 1 hour, and the resulting solid was collected by filtration, followed by drying under reduced pressure.The obtained solid was dissolved in a mixture of chloroform (100 ml) and ethanol (1 ml) while heating to reflux. Themixture was cooled to room temperature and then hexane (100 ml) was added thereto. The resulting solid was collectedby filtration, followed by drying under reduced pressure, thereby obtaining (5-bromo-1H-benzimidazol-2-yl){4-[4-(trifluoromethyl)benzyl]piperazin-1-yl}methanone (1.4 g) as a solid.

The synthetic route of 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; NAGASHIMA, Takeyuki; (29 pag.)EP3231424; (2017); 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. 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, A new synthetic method of this compound is introduced below., Recommanded Product: (1-Methyl-1H-imidazol-5-yl)methanol

General procedure: The reaction was performed in 2 batches. In a sealed tube, cyanomethylenetributyl phosphorane (9.28 mL, 35.40 mmol) was added to a solution of 3-methyl-5-nitro-lH- pyrazole (1.50 g, 1 1.80 mmol) and 3-hydroxymethyl-3-methyloxethane (3.53 mL, 35.40 mmol) in toluene (100 mL). The solution was heated at 60 ¡ãC for 18 h. The 2 batches were combined and the solvent was evaporated in vacuo. The residue (black oil) was purified by column chromatography on silica gel (irregular SiOH, 15-40 muiotaeta, 330 g, liquid loading on DCM, mobile phase: heptane/EtOAc, gradient from 90: 10 to 50:50). The fractions containing the product were combined and evaporated to dryness to give 3.95 g of intermediate 303 (79percent yield, orange oil) directly used as it in the next step.

The synthetic route of 38993-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (472 pag.)WO2018/2217; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 40644-16-4,Some common heterocyclic compound, 40644-16-4, name is 4-Bromo-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H5BrN2O, 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 3: 4-(4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-1 ,3-dihydro-benzoimidazol- 2-one To a solution of 4-bromo-1 ,3-dihydro-benzoimidazol-2-one (701 mg, 3.29 mmol) in dimethyl sulfoxide (2 ml_) was added potassium acetate (803 g, 10.9 mmol), 1,1′-bis(diphenyl phosphino) ferrocene palladium chloride (PdCI2 (dppf)) (134 mg, 0.16 mmol) and bis(pinacolato) diboron (1.67 g, 6.58 mmol). The mixture was degassed and heated in a microwave oven for 30 minutes at 150 0C. The solvent was filtered through a pad of celite, water (60 ml_) was added and the product was extracted with EtOAc (3 x, 30 ml_). The combined organic extracts were dried over Na2SO4 (sodium sulfate), and the solvent removed to provide crude 4-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-1 ,3-dihydro-benzoimidazol-2-one which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1H-benzo[d]imidazol-2(3H)-one, its application will become more common.

Reference:
Patent; WYETH; WO2009/111260; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 17289-19-9, These common heterocyclic compound, 17289-19-9, name is Methyl 1-methyl-1H-imidazole-4-carboxylate, 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 methyl 1 -methyl-1 H-imidazole-4-carboxylate (14.3 mmol, 2 g) in CCI4 (40 ml_), NBS (15.3 mmol, 2.72 g) and AIBN (0.715 mmol, 1 17 mg) were added. The reaction mixture was stirred 4h at 605C and then cooled to room temperature. The solvent was evaporated. The reaction crude was purified by flash chromatography on silica gel using an elution of 8% methanol in ethyl acetate to afford methyl 2-bromo-1 -methyl-1 H-imidazole-4-carboxylate (529 mg, Yield: 17%). 1 H NMR (400 MHz, CDCI3) delta 7.59 (1 H, s), 3.91 (3H, s), 3.67 (3H, s) LC-MS: tR = 1 .60 [M+H] + = 219/221 (method 3)

The synthetic route of 17289-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; DRACONIS PHARMA, S.L.; LABORATORIOS DEL DR. ESTEVE, S.A.; AGUILAR, Nuria; FERNANDEZ, Joan, Carles; TERRICABRAS, Emma; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/149997; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

16042-25-4, name is 2-Imidazolecarboxylic acid, 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. Application In Synthesis of 2-Imidazolecarboxylic acid

) A/-(3,5-Difluorophenyl)-1 H-imidazole-2-carboxamideTo a solution of 1 /-/-imidazole-2-carboxylic acid (2.50 g, 22.3 mmol) in DMF (30 mL) were added 3,5-difluoroaniline (2.23 mL, 22.3 mmol), EDC-HCI (6.41 g, 33.46 mmol) and HOBt (4.52 g, 33.46 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuum and the crude was dissolved in dichloromethane. The solution was washed with a diluted aqueous solution of potassium carbonate, dried over sodium sulphate, filtered and concentrated. 2.75 g (55% yield) of the title compound were obtained as a solid.LRMS (m/z): 224 (M+1 )

The synthetic route of 16042-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; BERNAL ANCHUELA, Francisco Javier; CARRASCAL RIERA, Marta; CATURLA JAVALOYES, Juan Francisco; GRACIA FERRER, Jordi; MATASSA, Victor Giulio; TERRICABRAS BELART, Emma; TALTAVULL MOLL, Joan; ERRA SOLA, Montserrat; WO2012/146666; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem