Category: imidazoles-derivatives

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. 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, A new synthetic method of this compound is introduced below., SDS of cas: 39070-14-9

A solution of triphosgene (62 mg, 0.21 mmol) in DCM (4.0 mL) was added to a stirred solution of A13 (prepared as described in: WO 2013/055987; 500 mg, 0.52 mmol) and Et3N (120 mg, 1.18 mmol) in DCM (20 mL) at 22 C. The mixture was stirred at that temperature for 2 h. A solution of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (112 mg, 0.71 mmol) in DCM (1 mL) was then added, followed by nBu2Sn(OAc)2 (3 drops). The resulting solution was stirred at 22 C for 16 h under N2 then was concentrated under reduced pressure. The residue was purified by prep-TLC (DCM/MeOH = 30/1) to give A14 as a yellow solid (180 mg, 31%). LCMS (condition A): RT = 1.11 min, m/z = 1136.9 [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:
Article; Dragovich, Peter S.; Broccatelli, Fabio; Chen, Jinhua; Fan, Peter; Le, Hoa; Mao, Weiguang; Pillow, Thomas H.; Polson, Andrew G.; Wai, John; Xu, Zijin; Yao, Hui; Zhang, Donglu; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5300 – 5304;,
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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C3H4N2

a. 4-(1H-Imidazol-1-yl)-nitrobenzene To a solution of 4-fluoronitrobenzene (25 g; ~ 0.18 mol) in 250 ml N,N-dimethylformamide was added imidazole (50 g; ~ 0.74 mol). The reaction mixture was stirred at 140C for 2 h, and then poured into ice-water to give the title compound as a precipitate. Yield: 32 g (~ 94%). M.p. 199-202C.

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; NOVO NORDISK A/S; EP698024; (1997); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 39021-62-0, A common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-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.

General procedure: A solution (0.05mol-%) of the appropriate furan-2-one (1 eq.) in dry diethyl ether (DEE) was mixed with the N-heterocyclic carbaldehyde (1, 2 or 3 eq.) under a nitrogen atmosphere at 0C. After stirring for 30min, excess dry diethylamine (4 eq.) was added dropwise. Stirring was continued for 30min. The solution was allowed to warm up over night and the product usually precipitated as fluffy powder. The precipitate was washed with cold DEE and dried in vacuo.

The synthetic route of 39021-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Uhrner, Fabian; Lederle, Felix; Namyslo, Jan C.; Gjikaj, Mimoza; Schmidt, Andreas; Huebner, Eike G.; Tetrahedron; vol. 73; 30; (2017); p. 4472 – 4480;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, 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 33468-69-8, category: imidazoles-derivatives

Sodium hydride (60 mass %) in 54 mineral oil (41.6 mg, 1.04 mmol) is added to a solution of 61 4-(trifluoromethyl)-1H-imidazole (96.3 mg, 0.694 mmol) in 56 DMF (5.0 mL) at 0 C. The mixture is stirred at room temperature for 30 minutes. 40 [3-[3-[6-(4-Isopropyl-1,2,4-triazol-3-yl)-2-pyridyl]-2-oxo-imidazolidin-1-yl]cyclobutyl] methanesulfonate (162.0 mg, 0.347 mmol) is added at room temperature, the mixture is heated to 90 C., and stirred for 17 hours. The reaction is quenched with water (20 mL) and the product is extracted with DCM (3×40 mL). The organic extracts are dried over Na2SO4 and concentrated in vacuo. The residue is purified by HPLC under the following conditions column: SunFire C18 5 mum, 30*100 mm, eluting with a gradient of 28%-43% of 57 ACN (0.1% FA) in 34 H2O (0.1% FA) over 10 minutes and stop at 17 minutes; flow rate: 30 mL/minutes. t(R) 7.5 minutes. The material is concentrated, dissolved in 21 water, and lyophilized to give the 62 title compound. ES/MS (m/z): 461.0 (M+1), 1H NMR (500 MHz, CDCl3) delta 8.36 (s, 1H), 8.33 (d, J=8.3 Hz, 1H), 7.93 (d, J=7.5 Hz, 1H), 7.81 (t, J=8.0 Hz, 1H), 7.65 (s, 1H), 7.43 (s, 1H), 5.58-5.52 (m, 1H), 4.90-4.85 (m, 1H), 4.72-4.69 (m, 1H), 4.09 (t, J=8.0 Hz, 2H), 3.65 (t, J=8.0 Hz, 2H), 3.11-3.05 (m, 2H), 2.76-2.70 (m, 2H), 1.57 (d, J=7.0 Hz, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Trifluoromethyl)-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; LIU, Lian Zhu; ZHANG, Haizhen; WANG, Xiaoqing; LIU, Gang; (14 pag.)US2019/71413; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, molecular formula is C8H6N2O, 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. Formula: C8H6N2O

General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0°C, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion using general procedure 3, 1-(2-aminoethyl)-N-[(3-chloropyridin-2-yl)methyl]-1 H- pyrazole-4-carboxamide dihydrochloride (261 ) (200 mg, 0.54 mmol), 1 H-benzimidazole-2-carbaldehyde (94.5 mg, 0.65 mmol) and DIPEA (0.38 ml, 2.16 mmol) in MeOH (8 ml) at room temperature for 16 h, followed by addition of NaBH^ (30.6 mg, 0.81 mmol) gave the title compound (127 mg, 56percent) as a pale green foam after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.17 (s, 1 H), 8.51 – 8.46 (m, 2H), 8.23 (s, 1 H), 7.92 (dd, J = 8.1 , 1.4 Hz, 1 H), 7.90 (s, 1 H), 7.58 – 7.41 (br m, 2H), 7.37 (dd, J = 8.1 , 4.7 Hz, 1 H), 7.17- 7.08 (m, 2H), 4.62 (d, J = 5.6 Hz, 2H), 4.23 (t, J = 6.2 Hz, 2H), 3.92 (br s, 2H), 2.98 (br s, 2H) HPLCMS (Method C): [m/z]: 410.2 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3314-30-5, its application will become more common.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 25676-75-9, The chemical industry reduces the impact on the environment during synthesis 25676-75-9, name is 4-Bromo-1-methylimidazole, I believe this compound will play a more active role in future production and life.

To a suspension of tert-butyl 4-({[2-amino-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-3-yl]oxy}methyl)piperidine-1 -carboxylate (I-55) (1 1 .08 g, 27.2 mmol), 4-bromo-1 -methyl-1 H-imidazole (5.26 g, 32.7 mmol), Cs2C03 (2 N in H20, 27.2 mL, 54.5 mmol) in toluene (50 mL) and EtOH (150 mL) was added Pd(PPh3)4 (4.72 g, 4.08 mmol). The mixture was thoroughly degassed with N2 three times and the brown suspension was then stirred at 85 C for 16 hr under N2. LCMS showed the desired product by mass had formed. The reaction mixture was concentrated under vacuum to give a residue, which was diluted with CH2CI2 (300 mL), washed with water (50 mL), brine (30 mL), dried over Na2S04 and concentrated to give the crude product which was purified twice by silica gel chromatography (0 to 5% MeOH in CH2CI2 followed by CH2CI2/MeOH = 1 /0 to 20/1 ) to give tert-butyl 4-({[2-amino-5-(1 -methyl-1 H-imidazol-4-yl)pyridin-3-yl]oxy}methyl)piperidine-1 -carboxylate (~ 5.9 g as a brown solid. ~ 90% purity). This material was diluted with EtOAc / CH2CI2 (5:1 , 60 mL) and heated to 60 C until a clear solution was obtained. Cooling the solution to 25 C with concomitant reduction of the volume under reduced pressure (~10 mL) lead to the appearance of a precipitate. The suspension was filtered, the filter cake was washed with EtOAc/petroleum ether (1 :1 , 10 mL) and dried under vacuum to give tert-butyl 4-({[2-amino-5-(1 -methyl-1 H-imidazol-4-yl)pyridin-3-yl]oxy}methyl)piperidine-1 -carboxylate (1-106) (4.38 g, 42%) as a purple solid.

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, 4-Bromo-1-methylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 4856-97-7,Some common heterocyclic compound, 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, molecular formula is C8H8N2O, 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 solution of 2a-2d (2 mmol), MnO2 (3.48 g, 40 mmol) was added to EtOAc (120 mL), then refluxedat 65 C for 1 h (monitored by TLC). Afterwards the solution was filtered, and concentrated in vacuoto give pure compounds 3a-3d (in 60%-76% yield) [17].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1H-Benzoimidazol-2-yl)methanol, its application will become more common.

Reference:
Article; Wang, Xing; Chen, Yong-Fei; Yan, Wei; Cao, Ling-Ling; Ye, Yong-Hao; Molecules; vol. 21; 11; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 41716-18-1, The chemical industry reduces the impact on the environment during synthesis 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, I believe this compound will play a more active role in future production and life.

Into a 50 mL round bottom flask equipped with a magnetic stir bar was placed 1-methyl-1H-imidazole-4-carboxylic acid (121 mg, 0.93 mmol), DMF (10 mL), ACN (20 mL), DIPEA(0.321 mL, 1.864 mmol), and HATU (378 mg, 0.99 mmol). This mixture was allowed tostirS mm at room temperature, afterwards 11(400 mg, 0.621 mmol) was added. The flaskwas sealed and allowed to stir at room temperature for 24 hours. The reaction mixture was reduced in volume, then poured into water (400 mL), and partitioned with ethyl acetate (3 x 100 mL). The organic layers were combined, dried over sodium sulfate, the solids were removed by filtration, and the solvent of the filtrate was removed underreduced pressure. The crude was purified by silica gel column chromatography using a n-heptane to ethyl acetate gradient. The best fractions were pooled and the solvent was removed under reduced pressure to afford 12. LC-MS ES mlz = 638.5; Rt: 2.34 mm, method B.

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-imidazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; JONCKERS, Tim Hugo Maria; MC GOWAN, David Craig; GUILLEMONT, Jerome Emile Georges; COOYMANS, Ludwig Paul; EMBRECHTS, Werner Constant Johan; BUYCK, Christophe Francis Robert Nestor; BALEMANS, Wendy Mia Albert; RABOISSON, Pierre Jean-Marie Bernard; (34 pag.)WO2017/89518; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 288-32-4, 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. 288-32-4, name is 1H-Imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step A. 1-Methoxymethyl-1H-imidazole To a solution of 1.06 g of imidazole (15.56 mmol) in 20 ml of THF at 0 C. was added 658 mg (16.45 mmol) of NaH (40% dispersion in oil) and the mixture was stirred at 0 C. for 30 mins.After this time, 1.2 ml (15.7 mmol) of chloromethyl methyl ether were added and the mixture was allowed to warm to room temperature and stirred for 14 h.After this time the reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride, allowed to warm to room temperature, and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and the filtrate was concentrated.The residue was purified by chromatography on silica gel (hexanes:EtOAc, 1:1) to give the title compound. 1H-NMR (CDCl3) delta 3.21 (s, 3H), 5.18 (s, 2H), 7.00 (d, J=19 Hz, 2H0, 7.54 (s, 1H).

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, 1H-Imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tularik Inc.; US2003/229093; (2003); 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. 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, A new synthetic method of this compound is introduced below., Application In Synthesis of (1H-Benzoimidazol-2-yl)methanol

To an ice-bath cooled solution of 18 (0.50 g, 3.38 mmol) in anhydrous DMF (7 ml) was added sodium hydride (NaH; 0.08 g, 3.38 mmol). After stirring at 0 °C for approx. 15 min (or after no more visible emergence of hydrogen), the mixture was allowed to warm up to room temperature and kept stirred for an additional 45 min. The mixture was then re-cooled to 0 °C, and benzyl chloride (0.39 ml, 3.38 mmol) was slowly added. The mixture was first stirred 1 h at 0C and then overnight at room temperature. The mixture was then quenched with cold water and crushed ice and extracted with DCM (2x). The combined organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (100percent DCM to DCM/MeOH; 97:3 stepwise gradient) to give the title compound as a yellow sticky solid (0.62 g). Yield: 77percent; mp: 157-159 °C; IR (Nujol): 3142, 2920, 2852, 1606, 1416, 1463, 1344, 1214, 1043, 856, 734; 1H NMR (300 MHz, CDCl3): delta 4.88 (s, 2H), 5.46 (s, 2H), 7.00-7.16 (m, 2H), 7.16-7.41 (m, 6H), 7.71 (d, 1H); MS (EI+) m/z: 238 [M+].

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; Darwish, Khaled M.; Salama, Ismail; Mostafa, Samia; Gomaa, Mohamed S.; Helal, Mohamed A.; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 157 – 172;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem