Tag: M.W=100-200

Some common heterocyclic compound, 30148-21-1, name is Ethyl 1-methyl-1H-imidazole-2-carboxylate, molecular formula is C7H10N2O2, 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. Application In Synthesis of Ethyl 1-methyl-1H-imidazole-2-carboxylate

Step 6a. A solution of ethyl 1 -methyl- lH-imidazole-2-carboxy late (2.0 g, 13 mmol) in 8 ml cone. H2SO4 and 8 ml cone. HNO3 was stirred for 3 hours at 70C. The solution was diluted with H2O, then adjusted to pH 7-8 with aq Na2C03 solution and extracted with DCM. The organic layer was concentrated and chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as yellow solid (0.9g, 34.7%). ESI- MS m/z = 200.20 [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 30148-21-1, its application will become more common.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; QIU, Yao-ling; LI, Wei; CAO, Hui; JIN, Meizhong; GAO, Xuri; PENG, Xiaowen; KASS, Jorden; OR, Yat, Sun; (84 pag.)WO2016/183266; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H3F3N2O

1,8-Diazabicyclo[5.4,0]undec-7-enium 5′-O-(tert-butyldiphenylsilyl)-3′-O-(tert-butyldimethylsilyl)uridin-3′-yl phosphonate (13u) (100 mumol) is dried by repeated coevaporations with dry pyridine and then dissolved in dry pyridine (1 mL). N,N’-bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BopCl; 500 mumol) is added, and the mixture is stirred for 5 min. To the mixture, a solution of amino alcohol (L-2) (100 mumol), which has been dried by repeated coevaportions with dry pyridine and dissolved in dry pyridine (1 mL), is added dropwise via syringe, and the mixture is stirred for 5 min under argon. 2′,3′-O-bis(tert-butyldimethylsilyl)uridine 9u is dried by repeated coevaporations with dry pyridine and dissolved in 100 mumol pyridine. Then the above mixture is added via cannula into the solution of 2′,3′-O-bis(tert-butyldimethylsilyl)uridine 9u (100 |imol). After 10 min, N-trifluoroacctyl imidazole (CF3COIm; 200 mumol) is added. After an additional 30 s, N,N’-dimethylthiuram disulfide (DTD; 120 mumol) is added. After an additional 3 min, the mixture is dried in vacuum. To the residue, cone NH3-EtOH (3:1, v/v, 10 mL) is added, and the mixture is stirred for 12 h, and then concentrated to dryness under reduced pressure. Then, the mixture is diluted with CHCl3 (5 mL), and washed with 0.2 M phosphate buffer (pH 7.0, 5 mL). The aqueous layers are back-extracted with CHCl3 (2 *5 mL). The combined organic layers are dried over Na2SO4, filtered, and concentrated to dryness under reduced pressure. The residue is purified by PTLC. The product is dissolved in CHCl3 (5 mL), washed with 0.2 M 1,8-diazabicyclo[5.4.0]undec-7-enium bicarbonate buffer (5 mL) and back-extracted with CHCl3 (2*5 mL). The combined organic layers are dried over Na2SO4, filtered, and concentrated to dryness to afford (Sp)-14uu.

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; ONTORII INCORPORATED; VERDINE, GREGORY L; MEENA, MEENA; IWAMOTO, NAOKI; (250 pag.)JP2015/205910; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, 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. COA of Formula: C5H3F3N2O

General procedure: The compound 6b (35.1 mg, 50 mumol) was dried by repeated coevaporations with dry MeCN (3 mL) under Ar. The thymidine 3?-O-oxazaphospholidine derivative 7t (75.5 mg, 0.10 mmol), which was dried in vacuo overnight, and a 0.3 M solution of CMPT 8 (0.5 mL), which was dried over MS3A overnight, were successively added, and the mixture was stirred for 20 min at rt under Ar. N-(Trifluoroacetyl)imidazole (17.0 muL, 0.15 mmol) and i-Pr2NEt (44.0 muL, 0.25 mmol) were added and the mixture was stirred for 30 min at rt. Then DTD (31.9 mg, 0.15 mmol) was added and the mixture was stirred for 50 min at rt. The mixture was then concentrated under reduced pressure, and the residue was dissolved in dichloromethane (5.0 mL). A 6 vol% DCA solution in dichloromethane (5.0 mL) and Et3SiH (1.2 mL, 7.5 mmol) were added and the mixture was stirred for 20 min at rt. The mixture was washed with saturated NaHCO3 aqueous solutions (3 ¡Á 10 mL). The aqueous layers were combined and back-extracted with dichloromethane (2 ¡Á 10 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by FSPE [1.6 cm column id, 4.8 g of fluorous silica gel, methanol-H2O 16 mL (80:20, v/v) then THF 25 mL] to give 14t, a, c or g as a colorless foam, which was analyzed by 31P NMR (Fig. 2). The 14t, a, c or g thus obtained was dissolved in ethanol (8.0 mL) and a 25% NH3 aqueous solution (40 mL) was added. The mixture was put in a sealed flask and heated at 55 C for 12 h while stirring. The mixture was then cooled to rt, concentrated under reduced pressure to ca. 20 mL The mixture was diluted with a 0.1 M ammonium acetate buffer (pH 7.0) (20 mL) and washed with CHCl3 (4 ¡Á 20 mL). The aqueous layer was then concentrated under reduced pressure. The residue was repeatedly lyophilized from distilled H2O to remove ammonium acetate to give crude the dinucleoside phosphorothioate (15t, a, c or g), which was analyzed by RP-HPLC [Senshu Pak PEGASIL ODS, 4 ¡Á 150 mm, linear gradient of 0-20% MeCN (60 min) in 0.1 M triethylammonium acetate buffer (pH 7.0), 50 C, 0.5 mL/min]. Authentic samples of 15t,a,c,g were synthesized via the solid-phase synthesis using the nucleoside 3?-O-oxazaphospholidines 7t,a,c,g as monomer units [8d].

The synthetic route of 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone has been constantly updated, and we look forward to future research findings.

Reference:
Article; Oka, Natsuhisa; Murakami, Ryosuke; Kondo, Tomoaki; Wada, Takeshi; Journal of Fluorine Chemistry; vol. 150; (2013); p. 85 – 91;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 78581-99-4, name is 5,6-Difluorobenzimidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 78581-99-4

A solution OF 2, 4, 6-TRICHLOROPYRIMIDIN (4.2 gram), 5,6-difluorobenzimidazole (3.6 gram) and K2CO3 (6.4 gram) in dimethyl sulfoxide (150 ml) was stirred at 40 C for 17 hours. The solution was taken up in water, and extracted three times with ethyl acetate. The ethyl acetate layers were combined, washed with brine, dried over magnesium sulfate, filtered, and the solvents were removed in vacuo. Silica gel chromatography (heptane/ethyl acetate 9/1) provided 1.2 g of the title compound.

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 78581-99-4.

Reference:
Patent; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2004/69829; (2004); 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. 112809-54-8, name is 4-((1H-Imidazol-1-yl)methyl)benzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C11H9N3

Step 3 4-[3-(tert-butyl-dimethyl-silanyloxy)-1-imidazol-1-yl-propyl]-benzonitrile 4-Imidazol-1-ylmethyl-benzonitrile (5.5 gms,30 mmol) was suspended in freshly distilled THF (150 mL) in dry glassware and stirred under argon in a -60 C. dry ice acetone bath then Lithium bis(trimethylsilyl)amide 1 molar in THF (33 mL) was added slowly. The mixture was stirred for 30 minutes and the temperature was reduced to -78 C. A suspension of tert-butyl-(2-iodo-ethoxy)-dimethyl-silane (9.5 gm, 33 mmol) in 20 mL of THF was cooled to -78 C. and added via cannula to the first solution and the resulting mixture was allowed to slowly warm to ambient temperature. After 16 hours the reaction was quenched by the addition of 10 mL of water and the solvent was removed in vacuo. The residue was suspended in ethyl acetate (200 mL) and extracted 2 times with saturated aqueous sodium bicarbonate (100 mL), then water (100 mL), then saturated sodium chloride solution (100 mL). The organic solvent was removed in vacuo and the residue was chromatographed on silica gel using 1:3 ethyl acatate: hexanes. The desired fractions were combined and the solvent was removed in vacuo to give the desired product. 1 H NMR (400 MHz, CDCl3) delta 7.64 (d, 2H); 7.59 (d, 1H); 7.25 (m, 2H); 7.10 (d,1H); 6.90 d,1H) 5.58 (m, 1H); 3.48 (m, 2H); 2.38 (m, 2H); 0.9 (m, 9H); 0.1 (m, 6H)

The synthetic route of 112809-54-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5939439; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89830-98-8, name is 5-Cyclopropyl-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 89830-98-8, Computed Properties of C6H8N2

2-bromo-4-(4-cyclopropyl-1H-imidazol-1-yl)pyridine (4a) To a mixture of 4-cyclopropyl-1H-imidazole (3.5 g, 32.37 mmol) and (2-bromopyridin-4-yl)boronic acid (7.18 g, 35.60 mmol) in MeOH (50 mL) was added Cu2O (463.12 mg, 3.24 mmol) in one portion at 20 C. under O2. The mixture was stirred at 20 C. for 10 min, then heated to 50 C. and stirred for 16 hours. LCMS showed one new peak with desired MS. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by flash silica gel chromatography (ISCO; 10 g SepaFlash Silica Flash Column, Eluent of 100% Ethyl acetate gradient 200 mL/min) to give 2-bromo-4-(4-cyclopropyl-1H-imidazol-1-yl)pyridine (4a). MS mass calculated for [M+1]+ (C11H10BrN3) requires m/z 264.0, LCMS found m/z 264.0; 1H NMR (400 MHz, MeOD) delta 8.39 (d, J=5.6 Hz, 1H), 8.32 (s, 1H), 7.94 (d, J=1.8 Hz, 1H), 7.66 (dd, J=2.0, 5.6 Hz, 1H), 7.53 (s, 1H), 1.93-1.85 (m, 1H), 0.93-0.84 (m, 2H), 0.82-0.71 (m, 2H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Terns, Inc.; XU, Yingzi; HALCOMB, Randall; KIRSCHBERG, Thorsten A.; ROMERO, F. Anthony; (117 pag.)US2019/315767; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

[2793] To a stirred solution of 994 (3.08 g, 20 mmol) in 15 ml of DMF at 0¡ã C. was added NaH (60percent in mineral oil, 0.80 g) portionwise. After stirring for several minutes, SEM-CI (3.54 ml, 20 mmol) was added and let the reaction stir overnight. Brine was added to the reaction and extracted with EtOAc. The organic layer was washed with water and brine, dried with MgSO4, filtered and concentrated under vacuum. Purified by flash elute column chromatography (CH2Cl2/MeOH, 50:1 to 20:1) to afford 4.54 g of yellow oil, compound 995.

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

Reference:
Patent; Schering Corporation; US2004/122018; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, 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 33543-78-1, HPLC of Formula: C6H8N2O2

To a suspension of ethyl lH-imidazole-2-carboxylate (40.01 g, 285.5 mmol) in dried THF (600 mL) was added sodium hydride (13.82 g, 345.5 mmol, 60 mass%) at 0 C. The mixture was stirred at room temperature for 1 h, and then cooled down to 0 C. To the mixture was added ( -(2,4-dinitrophenyl)hydroxylamine (80.00 g, 401.8 mmol) in portions, and then the resulted mixture was stirred at room temperature overnight. The mixture was diluted with water (600 mL), and the resulted mixture was extracted with EA (600 mLchi10). The combined organic layers were dried over anhydrous Na2SC>4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EA/PE (v/v) = 1/2 to 1/1 to 2/1) to afford the title compound as a brown solid (37.6 g, yield 85%).MS (ESI, pos. ion) m/z: 156.1 [M + H]+;NMR (400 MHz, CDCb) delta (ppm): 7.19 (s, IH), 7.07 (s, IH), 5.82 (s, 2H), 4.43 (q, J = 7.1 Hz, 2H), 1.44 (t, J = 7.1 Hz, 3H).

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, Ethyl 1H-imidazole-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Xiaobo; LI, Mingxiong; ZHANG, Tao; HU, Haiyang; WU, Yanjun; (139 pag.)WO2018/169700; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 4278-08-4, name is 2-(4-Fluorophenyl)-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 2-(4-Fluorophenyl)-1H-imidazole

To a stirring mixture of Intermediate R -1 (0.338 mmol) in DMSO, 2-(4- fluorophenyl)-lH-imidazole (0.67 mmol) is added. The reaction mixture is placed in a 120 C oil bath for 2 h. The crude mixture is directly loaded and purified by silica gel chromatography to give the coupled nitro ester. To a stirring mixture of the coupled nitro ester in MeOH, Pt/C (42 mg) is added and the reaction mixture is placed under 1 atm of hydrogen for 2 h. The hydrogen balloon is removed and VO(acac)2 is added. This reaction mixture is placed under 1 atm of hydrogen overnight. The crude mixture is filtered through a plug of Celite and the plug is washed several times with EtOAc. The filtrate is concentrated under reduced pressure. This cyclized compound is then reacted similarly to the final step of Example 13 with either trimethyl ortho formate or trimethylorthoacetate to give the title compounds.

The synthetic route of 4278-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; NEITZ, R., Jeffrey; TROUNG, Anh, P.; GALEMMO, Robert, A.; YE, Xiaocong, Michael; SEALY, Jennifer; ADLER, Marc; BOWERS, Simeon; BEROZA, Paul; ANDERSON, John, P.; AUBELE, Danielle, L.; ARTIS, Dean, Richard; HOM, Roy, K.; ZHU, Yong-liang; WO2012/48129; (2012); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2034-23-3, These common heterocyclic compound, 2034-23-3, name is 5-Chloro-1H-benzo[d]imidazol-2(3H)-one, 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 5-methyl-1,3-dihydrobenzimidazol-2-one (1.00 g, 6.84 mmol) and phosphorous oxychloride (9.54 mL, 103 mmol) was stirred for 1.5 h at 95 C. After being cooled to ambient temperature, the reaction mixture was carefully added to a mixture of saturated NaHCO3 aq. (60 mL) and ethyl acetate (60 mL). The separated organic layer was washed with water, brine, and dried over MgSO4. After filtration, the filtrate was evaporated in vacuo, The resulting precipitates were collected by filtration, and successfully washed with isopropyl ether to give 2-chloro-5-methyl-benzimidazole (1.74 g, 58.9 %).

Statistics shows that 5-Chloro-1H-benzo[d]imidazol-2(3H)-one is playing an increasingly important role. we look forward to future research findings about 2034-23-3.

Reference:
Article; Nakao, Syuhei; Mabuchi, Miyuki; Shimizu, Tadashi; Itoh, Yoshihiro; Takeuchi, Yuko; Ueda, Masahiro; Mizuno, Hiroaki; Shigi, Naoko; Ohshio, Ikumi; Jinguji, Kentaro; Ueda, Yuko; Yamamoto, Masatatsu; Furukawa, Tatsuhiko; Aoki, Shunji; Tsujikawa, Kazutake; Tanaka, Akito; Bioorganic and Medicinal Chemistry Letters; vol. 24; 4; (2014); p. 1071 – 1074;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem