Category: imidazoles-derivatives

Related Products of 360-97-4,Some common heterocyclic compound, 360-97-4, name is 4-Amino-1H-imidazole-5-carboxamide, molecular formula is C4H6N4O, 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.

A mixture of 0.252 g 5-amino-1H-imidazole-4-carboxamide(Acros Organics, 2 mmol) and 0.764 g 3Me-STB(2 mmol) in 10 cm3 MeOH was heated to reflux for 3 h.The reaction mixture was left at room temperature (24 h)and filtered. The formed solid was crystallized from 5 cm3MeOH to give 0.37 g (69 %) light brown crystals of 3a.M.p.: [410 C; 1H NMR (500 MHz, DMSO-d6):d = 10.43 (s, 1H, NH), 10.19 (s, 1H, C(20)-OH), 10.16(s, 1H, C(40)-OH), 8.26 (s, 1H, C(2)-H), 7.37 (s, 1H,C(60)-H), 6.43 (d, J = 8.90 Hz, 1H, C(50)-H), 2.03 (s, 3H,CH3) ppm; 13C NMR (125 MHz, DMSO-d6): d = 161.7,158.6, 154.7, 136.9. 134.9, 133.4, 126.1, 122.6, 111.2,110.1, 107.4, 8.0 ppm; MS (70 eV): m/z (%) = 275 (M?,100), 274 (5), 259 (5), 192 (20), 167 (26), 151 (25), 110(5), 68 (16).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-1H-imidazole-5-carboxamide, its application will become more common.

Reference:
Article; Matysiak, Joanna; Skrzypek, Alicja; Niewiadomy, Andrzej; Juszczak, Malgorzata; Langner, Ewa; Lemieszek, Marta; Rzeski, Wojciech; Karpiska, Monika M.; Walczak, Katarzyna; Monatshefte fur Chemie; vol. 146; 8; (2015); p. 1315 – 1327;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 705-09-9, A common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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.

A mixture of 2-difluoromethyl-lH-benzimidazole (0.168 g), 4,6-dichloro- 2-morpholinopyrimidine (0.233 g), sodium bicarbonate (0.168 g) and DMA (5 ml) was stirred under nitrogen and heated to 90C for 20 hours. The resultant mixture was cooled, filtered and the filtrate was evaporated. The resultant product was purified by column chromatography on silica using increasingly polar mixtures of ethyl acetate in methylene chloride as eluent. The solid so obtained was washed with a 1 : 1 mixture of isohexane and diethyl ether. There was thus obtained 6-chloro-4-(2-difluoromethylbenzimidazol- 1 -yl)-2-morpholinopyrimidine (0.075 g); NMR Spectrum: (DMSOd6) 3.7 (m, 4eta), 3.78 (m, 4H), 7.2 (s, IH), 7.39-7.72 (m, 3H), 7.84 (d, IH), 7.9 (d, IH); Mass Spectrum: M+H+ 366.

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:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; HILL, George, Beresford; PASS, Martin; WO2008/32089; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 401567-00-8,Some common heterocyclic compound, 401567-00-8, name is 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, molecular formula is C8H4ClN3, 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.

A mixture of 2-chloro-1H-benzimidazole~5-carbonitrile (3.0 g, 17 mmol, 1.0 eq), (2S)-2-[(4-tert-0 butylphenoxy)methyl]oxirane (1-2) (3.5 g, 19 mmol, 1.1 eq) and cesium carbonate (0.10 g, 0,31 mmol, 0.020 eq) were heated under microwave irradiation at 130 C for 45 minutes. Ethyl acetate was added (200 ml) and the organic layer was washed with water (50 ml) and dried over sodium sulfate. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) followed by purification by super critical fluid chromatography (ChiraiPak AS-5 H, 21x250mm, 90/10 CO2/Methanol, 70 ml/min) to separate regioisomers and yield (2S)-2- ( { [tert-butyl(dimethyl )si Iy I ]oxy } methy l)-2 , 3 -dihydro [1,3] oxazolo [3 ,2 -a] benzi midazole-7 – carbonitrile (1-3) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.80 (s, 1H), 7.42 (d, 1H, J = 8.2 Hz), 7.19 (d, 1H, J = 8.2 Hz), 5.51-5.44 (m, 1H), 4.35-4.26 (m, 2H), 4.10 (dd, 1H, J – 1 1.8, 3.8 Hz), 3.95 (d, 1H, J – 3.1 Hz), 0.76 (s, 9 H), 0.00 (s, 6 H). LRMS m/z (M+H) 330.0 found,0 330.2 required. The alternative regioisomer (1-4) was also isolated and characterized.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2009/140163; (2009); 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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., SDS of cas: 68282-53-1

4-[(3-Carbamoylphenyl)(piperidin-4-yliden e)methyl]-N, N-dimethylbenzamide (40 mg, 11 mmcl) and4-methyl-IH-imidazole-5-carbaldehyde (13.3 mg, 0.12 mmol) were dissolved in dichloroethane (1.5mL). Acetic acid (6.3 pL, 0.11 mmol) was added and the reaction was stirred for 10 minutes at room temperature before NaBH(OAc)3 (37.3 mg, 0.18 mmcl) was added. The reaction mixture was stirred at room temperature for 2 days. Methylene chloride (1 mL) was added and the mixture was washed with water (1 mL). The water phase was extracted with methylene chloride (1 mL x 3). The combined organic phases were dried with Na2SO4, filtered and evaporated. The crude product waspurified by preparative HPLC (10 to 50% CH3CN in 50 mM NH4HCOS(aq)) to give the title compound (14 mg, 28% yield) as a white solid. MS ESI m/z 458 [M+H].

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:
Patent; PHARMNOVO AB; VON MENTZER, Bengt; STARKE, Ingemar; BRANDT, Peter; (20 pag.)WO2016/99393; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 934-22-5, A common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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.

General procedure: A dry 50 mL flask was charged with 2-halogenated aromatic aldehyde 1 (1.0 mmol), 1H-benzo[d]imidazol-5-amine (0.133 g,1.0 mmol), cyclohexane-1,3-diones (1.0 mmol), CuI (10 mg), L-proline(6 mg), Cs2CO3 (650 mg) and dioxane (10 mL). The reaction mixture was stirred at reflux for 10-18 h. After completion of the reaction, as indicated by TLC, the solid was filtered off by a fast and hot filtration, and the products of 4 were obtained as pale yellow powder or crystals, when the mixture was allowed to cool down to room temperature.

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; Li, Chao; Zhang, Wen-Ting; Wang, Xiang-Shan; Tetrahedron; vol. 70; 46; (2014); p. 8919 – 8924;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 13275-42-8, The chemical industry reduces the impact on the environment during synthesis 13275-42-8, name is 2-(2-Bromophenyl)-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, Cu(OAc)2 (18 mg, 0.1 mmol, 20 mol%), NaOEt (68 mg, 1.0 mmol), 1,10-phenanthroline monohydrate (40 mg, 0.2 mmol, 40 mol%), 2-(2-bromophenyl)-1H-benzo[d]imidazole 4 (0.5 mmol), and N-heterocycle 2 (0.5 mmol). The Schlenk tube was evacuated and backfilled with O2 (this procedure was repeated three times). Under a counter flow of O2, DMF (2.0 mL) was added using a syringe. The reaction mixture was stirred at 140 C for 24 h. After the reaction was completed, the mixture was extracted with dichloromethane (3 × 15 mL), and then the organic layer was washed with brine (3 × 10 mL) and dried over anhydrous Na2SO4. Subsequently, the solvent was removed, and the product was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol as the eluent, affording the pure products

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-(2-Bromophenyl)-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Dingben; Huang, Ling; Yang, Jianguo; Ma, Junna; Zheng, Yingying; Luo, Yi; Shen, Yang; Wu, Jiashou; Feng, Chao; Lv, Xin; Tetrahedron Letters; vol. 59; 21; (2018); p. 2005 – 2009;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 13435-22-8,Some common heterocyclic compound, 13435-22-8, name is 1-Butyl-2-methyl-1H-imidazole, molecular formula is C8H14N2, 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.

Ex is of a 1-butyl-2-methyl-3(propyl-3-sulfonyl) imidazolium 1-Butyl-2-methylimidazol (710 mg, 0.9 mmol, 1 equivalent) was dissolved in 10 ml toluene and propanesultone (610 mg, 0.9 mmol, 1 equivalent) was added. The clear solution was heated at reflux temperature for 3h at which time a some withe precipitate was formed. The reaction mixture was cooled to room temperature and the white suspension was then filtered and washed with 5 ml toluene. The white solid was dried under high vacuum at 60C for 4 h, yielding the desired product (89 mg, 38% yield). H NMR analysis confirms the structure and a purity of >98 %. Melting point by DSC: 160 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Butyl-2-methyl-1H-imidazole, its application will become more common.

Reference:
Patent; ECOLE D’INGENIEURS ET D’ARCHITECTES DE FRIBOURG; MARTI, Roger; VANOLI, Ennio; AEBY, Sandrine; FISCHER, Fabian; HAPPE, Manuel; WO2013/8172; (2013); 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, A new synthetic method of this compound is introduced below., Formula: C4H6N4O2

In a 1,000-liter reactor was charged 320 kg of water, Heated to reflux, 71 kg of glycoluril and 58 kg of 50% glyoxal were successively added, Stirring to clear, In the refluxing state, 500 L of a sodium hydroxide solution (8 mol / l) was rapidly added dropwise, After completion of the dropwise addition, The refluxing reaction was continued for 8 hours. Close the heating,When the temperature naturally cool to room temperature,45 kg of chlorine gas was introduced into the reaction system,After completion of the reaction,Concentrated hydrochloric acid was added to adjust the pH to 1,Stirring was reduced to room temperature,After 2 hours,Obtain crude orotic acid.In the 2000-liter reactor, the crude orotate was added and 600 kg of water was added. After boiling, add the concentrated ammonia to dissolve, then add 5 mol / L sulfuric acid to adjust the pH to weak acidity, add activated carbon to boil for 30 minutes, filter it hot, adjust the pH to 1 with concentrated sulfuric acid, Dry, get whey acid finished 25.7 kg, yield 33%, purity 99.9%.

The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Baishixing Science and Technology Industry Co., Ltd.; Shi, Changqing; (6 pag.)CN106187918; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 106429-59-8,Some common heterocyclic compound, 106429-59-8, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, molecular formula is C8H6N2O2, 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 stirred mixture of intermediate 62 (120 mg, 0.32 mmol), 2-oxo-2,3-dihydro-1Hbenzo[d]imidazole-S-carbaldehyde (CAS: 106429-59-8) (104 mg, 0.64 mmol) and TiG-PrO)s (92 mg, 0.32 mmol) in DCE/DMSO(6 mL/2 mL) at 0 C was added NaBH(OAc); (205 mg, 0.97 mmol) in portions. The reaction mixture was stirred at room temperature overnight. The reaction was quenched with aq. NaHCOsand the resultant was extracted with DCM. The combined organic extracts were washed with brine, dried over anhydrous Na2SQOuq,filtered and concentrated. The residue was purified by prep-HPLC (Waters 2767/Qda, Column: Waters Xbridge 19*150 mm 10 um, Mobile Phase A: H,O (0.1% TFA), B: ACN) to give Compound 117 (22 mg TFA salt, yield: 13%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 57090-88-7, 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 57090-88-7 as follows.

a) 1-(2-Trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile A flask charged with imidazole-4-carbonitrile (0.5 g, 5.2 mmol) (Synthesis, 677, 2003), 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl) (0.95 mL, 5.3 mmol), K2CO3 (1.40 g, 10.4 mmol), and acetone (5 mL) was stirred for 10 h at RT. The mixture was diluted with EtOAc (20 mL) and washed with water (20 mL) and brine (20 mL) and the organic layer dried over MgSO4. The crude product was eluted from a 20-g SPE cartridge (silica) with 30percent EtOAc/hexane to give 0.80 g (70percent) of the title compound as a colorless oil. Mass spectrum (CI (CH4), m/z) Calcd. for C10H17N3OSi, 224.1 (M+H). found 224.1.

According to the analysis of related databases, 57090-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Illig, Carl R.; Ballentine, Shelley K.; Chen, Jinsheng; Meegalla, Sanath K.; Rudolph, M. Jonathan; Wall, Mark J.; Wilson, Kenneth J.; Desjarlais, Renee L.; Manthey, Carl L.; Molloy, Christopher J.; US2008/51402; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem