Month: January 2021

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

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

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

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. 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

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

Reference of 6160-65-2, 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 6160-65-2 as follows.

At 0C, a solution of 1,1′-thiocarbonyldiimidazole (206 mg, 1.10 mmol) in DCM (3 mL) was added dropwise 4-(3-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester (160 mg, 0.58 mmol) in DCM (2 mL) and the mixture was stirred at room temperature for 3 hours. The reaction mixture was cooled again to 0C and a solution of ammonia in MeOH 7N (2 mL) was added dropwise. The reaction mixture was stirred at room temperature for 16 hours. Water was added and extracted with DCM. Purification by flash chromatography (silica gel, gradient to hexanes to 50% acetone). The desired product was obtained as a white foam (180 mg, 93% yield).

According to the analysis of related databases, 6160-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S. A.; CUEVAS CORDOBES, FELIX; ALMANSA ROSALES, CARMEN; GARCIA LOPEZ, MONICA; (299 pag.)TW2016/27300; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, 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 3012-80-4, Product Details of 3012-80-4

General procedure: The equimolar aldehyde 3a?3d (1 mmol) and substituted phenylhydrazine 5a?5s (1 mmol) weremixed in CH3OH (10 mL) and stirred at room temperature [18]. After about 2 h, the reaction wascompleted (monitored by TLC). The residual crude was purified via silica gel column chromatogramusing a gradient mixture of petroleum ether and ethyl acetate to obtain the pure target compounds6a?6ai (in 45?80percent yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, and friends who are interested can also refer to it.

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

Electric Literature of 68282-53-1,Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

Example 42 (Z)-1,3-Dihydro4-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-5-nitro-2H-indol-2-one (OO) STR68 To a solution of 1,3-dihydro4-fluoro-5-nitro-2H-indol-2-one (1 g, 5 mmol) in MeOH (10 mL) (Starting Material 10), was successively added, at r.t., 4-methyl-5-imidazolecarboxaldehyde (612 mg, 5.5 mmol) (Aldrich) and tetrabutyl ammonium hydroxide (11 mL, 1.0 M solution in MeOH)(Aldrich). The mixture was stirred at r.t. for 4 h. The resulting greenish precipitate was collected by suction filtration, washed with ether and air dried to yield (Z)-1,3-dihydro-4-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-5-nitro-2H-indol-2-one as a green powder. (Yield 1.14 g, 79%).

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

Reference:
Patent; Hoffmann-La Roche Inc.; US6153634; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 10040-96-7, 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. 10040-96-7 name is 1-(4-Bromophenyl)imidazole, 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.

22.0g of 1- (4-bromophenyl) -1H-imidazole,27.8g of 10-iodocamphor and 50mL of N, N-dimethylformamide were sequentially added to a three-necked flask equipped with a stirrer, a thermometer and a condensing reflux device.The reaction is carried out at 130 C, and the reaction takes about 4 hours to complete the reaction of one of the raw materials.After cooling, 50 mL of ethyl acetate was added to precipitate the product, and the crude product of camphoryl imidazole iodide was filtered to obtain the target compound by recrystallization from ethanol. The product characterization data is as follows: 80% yield,

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

Reference:
Patent; Nanjing Forestry University; Wang Shifa; Bian Tiancen; Zhao Yuxun; Xu Xu; Yang Yiqin; Gu Wen; (13 pag.)CN110272344; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem