Month: June 2021

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. 1262035-61-9, name is 5-Bromo-1-cyclopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 1262035-61-9

A microwave vial was charged with 5-bromo-1-cyclopropyl-1H-imidazole (40 mg, 0.21 mmol), 3-methoxy-1-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)- 1H-pyrazole-4-carboxamide (75 mg, 0.21 mmol), cesium carbonate (137 mg, 0.42 mmol) and Pd(dppf) G3 (20 mg, 0.02 mmol). Dioxane (1.5 mL) and water (75 muL) were added. The vial was purged with N2, sealed and irradiated in a biotage microwave at 120 C for 1 h. After this time he volatiles were removed under reduced pressure and the resulting black residue was taken up in DMSO and subjected to prep-HPLC (using a Sunfire Prep C18 OBD, 5mum 30x50mm column and using 95% water/5% MeCN (initial conditions) to 50% water/50% MeCN over 20 minutes in 0.1% TFA as the mobile phase at a flow rate of 50 mL/min). The fractions containing product were combined, evaporated to dryness and the resulting residue was dissolved in DCM (20 mL) and washed with satd. NaHCO3 (10 mL). The organic layer was separated, dried over Na2SO4, filtered and concentrated to give the title compound (28 mg, 40%) as a white solid. 1H NMR (400 MHz, CDCl3) d ppm 8.53 (s, 1H), 8.01 (t, J=1.8 Hz, 1H), 7.79 (s, 1H), 7.57 (d, J=0.8 Hz, 1H), 7.46 – 7.41 (m, 1H), 7.36 (t, J=7.8 Hz, 1H), 7.25 (td, J=1.4, 7.8 Hz, 1H), 7.11 (d, J=1.3 Hz, 1H), 4.09 (s, 3H), 3.78 (s, 3H), 3.42 (tt, J=3.7, 7.2 Hz, 1H), 1.06 – 0.98 (m, 2H), 0.90 – 0.82 (m, 2H). MS (ESI): 338.1 [M + H]+.v

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; BIOGEN MA INC.; GONZALEZ LOPEZ DE TURISO, Felix; XIN, Zhili; HIMMELBAUER, Martin; JONES, John, H.; (147 pag.)WO2020/36949; (2020); 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. 31722-49-3, name is 1H-Imidazole-2-carbonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C4H3N3

l,8-Diazabicyclo[5.4.0]undec-7-ene (7.28 mL, 48.75 mmol) was added to a stirred solution of (R)-tert-butyl-4-(5-bromo-2-fluorophenyl)-4-methyl-l,2,3-oxathiazolidine- 3-carboxylate 2,2-dioxide (10 g, 24.4 mmol) and lH-imidazole-2-carbonitrile (2.61 g, 28.03 mmol) in acetonitrile (80 mL). The mixture was stirred at 90 C for 18 hours and then diluted with HCl (1 M) and extracted with DCM. The organic layer was separated, dried (Na2S04), filtered and the solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo to yield (R)-tert-buty [ 1 -(5-bromo-2-fluorophenyl)-2-(2-cyano- lH-imidazol- 1 -yl)- 1 -methylethyljcarbamate (10 g, 97 % yield) as a sticky solid.

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; JANSSEN PHARMACEUTICA NV; TRABANCO-SUAREZ, Andres, Avelino; DELGADO-JIMENEZ, Francisca; VEGA RAMIRO, Juan, Antonio; TRESADERN, Gary, John; GIJSEN, Henricus, Jacobus, Maria; OEHLRICH, Daniel; WO2012/85038; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 827-43-0, These common heterocyclic compound, 827-43-0, name is 4-Methyl-2-phenyl-1H-imidazole, 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 mixture of bicyclic olefin 2a (0.2083 mmol, 1.75 equiv),2-phenylimidazole (0.1191 mmol, 1.0 equiv), [RhCl2Cp*]2(0.0029 mmol, 2.5 mol%), and Cu(OAc)2·H2O (0.1338mmol, 1.5 equiv) were weighed in a Schlenk tube anddegassed for 10 min. Anhydrous MeCN (2 mL) was added,and the reaction mixture was purged with argon and allowedto stir at 80 C for 12 h. The solvent was evaporated invacuo, and the residue was purified with columnchromatography (silica gel, 100-200 mesh) using anEtOAc-hexane mixture. Mono- and biscyclopentenylfunctionalizedaza heteroaromatics were obtained in 48%and 39% yields, respectively.

Statistics shows that 4-Methyl-2-phenyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 827-43-0.

Reference:
Article; Prakash, Praveen; Aparna; Jijy; Santhini; Varughese, Sunil; Radhakrishnan; Synlett; vol. 25; 2; (2014); p. 275 – 279;,
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. 68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Quality Control of 2-Phenyl-1H-imidazole-4-carbaldehyde

COMPOUND 12.1.63: 1-{4-[(DIETHYLAMINO)CARBONYL]PHENYL}-6- METHOXY-2-[(2-PHENYL-lH-IMIDAZOL-5-YL) METHYLl-1. 2*3. 4- TETRAHYDROISOQUINOLIN-7-YL DIMETHYLSULFAMATE; INTERMEDIATE 8.3. 1 (53 mg, 0.11 mmol) and2-phenylimidazole-4-carbaldehyde (48 mg, 0. 28 mmol) were dissolved in 1, 2-dichloroethane (5 mL) and stirred for 10 min at room temperature. Sodium triacetoxyborohydride (120 mg, 0.55 mmol) was added and the mixture was stirred for 18 h. Tosylhydrazine resin (0.37 g, 1.5 mmol/g) and DCM (5 mL) were added and the mixture was stirred for another 2 h. The resin was filtered off and washed twice with DCM. The filtrate was washed with 1 M aqueous sodium hydroxide solution, water, and brine, dried, and evaporated. Flash chromatography of the residue yielded the desired product (36 mg, 0.06 mmol, 53 %). ‘H NMR (500 MHz, DMSO): 1.02, 1.15 (2 brs, 6H), 2.72 (s, 6H), 3.04 (m, 2H), 3.18 (m, 3H), 3.40 (m, 3H), 3. 82 (s, 3H), 5. 38 (s, 1H), 6.42 (s, 1H), 7.18 (s, 1H), 7.40 (m, 4H), 7. 58 (m, 4H), 7.59 (s, 1H), 7.98 (d, J 8.0 Hz, 2H). (+) LRESIMS mlz 618 [M+H] +.

The synthetic route of 68282-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 172499-76-2, name is Ethyl 3-(1H-imidazol-2-yl)propanoate, molecular formula is C8H12N2O2, 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. category: imidazoles-derivatives

General procedure: A suspension of tBuOK (1.1 equiv. or 2.2 equiv.) and the imidazole derivative (1.0 equiv.) in DMF (6 mL/mmol) was stirred at rt for 1 h. The reaction mixture was treated with the corresponding alkyl bromide or alkyl mesylate (1.3 equiv. or 2.0 equiv.) and the temperature was raised up to 60 C and stirred at this temperature for 72 h. The solution was then diluted with EtOAc (20 mL/mmol) and washed three times with brine and H2O. The organic layers were dried over MgSO4, filtered, and concentrated. The crude product was purified by CC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 172499-76-2, its application will become more common.

Reference:
Article; Kerscher-Hack, Silke; Renukappa-Gutke, Thejavathi; Hoefner, Georg; Wanner, Klaus T.; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 852 – 880;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 17286-47-4, name is 2-(1H-Imidazol-2-yl)ethanamine dihydrochloride, molecular formula is C5H11Cl2N3, 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: C5H11Cl2N3

To a mixture of 3 -chloro-2-(4-fluorophenyl)quinoxaline-6-carbonyl chloride ( 1.03 g, 3.21 mmol, prepared according to Example 44, Route 1, Step 3) in N,N-dimethylacetamide (45 mL) was added 2-(lH-imidazol-2-yl)ethanamine dihydrochloride (709 mg, 3.85 mmol) and TEA (2.24 mL, 16.1 mmol) and the resulting mixture was stirred at room temperature overnight. The reaction was then poured into saturated sodium bicarbonate (50 mL). Water (50 mL) and ethyl acetate (200 mL) were added. The layers were separated and the aquous layer was extracted with ethyl acetate (100 mL). The combined organic layers were washed with water (5 x 50 mL), dried, filtered and concentrated in vacuo. Silica gel chromatography gave N-(2-( 1 H-imidazol-2-yl)ethyl)-3 -chloro-2-(4-fluorophenyl)quinoxaline-6- carboxamide (541 mg, 42%). LCMS (ESI+): m/z = 396.1 (M+H). H NMR (400 MHz, OMSO-d6) delta 11.86 (bs, 1H), 9.06 (t, J= 5.6 Hz, 1 H), 8.55 (d, J= 1.6 Hz, 1 H), 8.30 (dd, J= 8.8, 1.6 Hz, 1 H), 8.27 (d, J= 8.8 Hz, 1 H), 7.96-7.93 (m, 2 H), 7.45-7.40 (m, 2 H), 6.92 (bs, 2 H), 3.68-3.62 (m, 2 H), 2.97-2.93 (m, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17286-47-4, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; GIGSTAD, Kenneth, M.; CARDIN, David, P.; HIRAYAMA, Takaharu; HIROSE, Masaaki; HU, Yongbo; KAKEI, Hiroyuki; LEE, Hong, Myung; MOTOYAJI, Takashi; NII, Noriyuki; SHI, Zhan; VYSKOCIL, Stepan; WATANABE, Hiroyuki; WO2015/161142; (2015); 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

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

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

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