Tag: M.W=100-200

3097-21-0, 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. 3097-21-0 name is 1,3-Dimethyl-1H-benzo[d]imidazol-2(3H)-one, 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.

Take 1,3-dimethyl-1,3-dihydro-2H-benzo [d] imidazol-2-one (1.0 g, 6.1 mmol),Add to chlorosulfonic acid and react at room temperature for 5 hours;After the reaction is completed, water is added to precipitate a solid, which is filtered with suction, recrystallized, and filtered with suction, and the filter cake is dried under infrared.A gray solid was obtained with a yield of 88%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dimethyl-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; China Pharmaceutical University; Sun Haopeng; Mo Jun; Li Qihang; Yang Hongyu; Chen Yao; Chen Tingkai; Li Qi; Guo Yan; Liu Zongliang; Feng Feng; Liu Wenyuan; (19 pag.)CN110776494; (2020); A;,
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10364-94-0, Name is (1H-Imidazol-1-yl)(phenyl)methanone, 10364-94-0, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

General procedure: To a solution of substrate (100 mg) in 2.5 mL MeCN (dry) and 0.15 mL DMF (dry) was added DBU(0.2 equiv.), and the mixture was allowed to stir at 50 C for 10 min. 1-Benzoylimidazole (1.1 equiv.) in 0.5 mL MeCN (dry) was added to the reaction mixture in two portions and it was allowed to stir at 50C for 8 h. MeCN was removed under reduced pressure and the resulting mixture was purified by flashcolumn chromatography (ethyl acetate/petroleum ether = 1:1 to 10:1) to afford benzoylated products.

Statistics shows that (1H-Imidazol-1-yl)(phenyl)methanone is playing an increasingly important role. we look forward to future research findings about 10364-94-0.

Reference:
Article; Lu, Yuchao; Hou, Chenxi; Ren, Jingli; Xin, Xiaoting; Xu, Hengfu; Pei, Yuxin; Dong, Hai; Pei, Zhichao; Molecules; vol. 21; 5; (2016);,
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Imidazole | C3H4N2 – PubChem

39021-62-0, 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 39021-62-0 as follows.

A mixture of (E)-4-(benzylideneamino) isobenzofuran-1(3H)-one (474 mg, 2 mmol) and 1-methyl-1H-imidazole-5-carbaldehyde (220 mg, 2 mmol) in ethyl propionate (20 mL) was cooled to 0 C. Then a solution of sodium ethoxide in ethanol [sodium (184 mg, 8 mmol) in ethanol (10 mL)] was added dropwise. After the addition, the mixture was stirred at room temperature for 3 hr. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (100 mL¡Á4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=5:1 to 3:7) to give ethyl 3-(1-methyl-1H-imidazol-5-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (170 mg, yield 23%). LC-MS (ESI) m/z: 376 (M+1)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 39021-62-0, and friends who are interested can also refer to it.

Reference:
Patent; LEAD THERAPEUTICS, INC.; US2010/35883; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 2302-25-2 as follows. 2302-25-2

Step 1: To a stirred mixture of DMF (15 mL) and NaH (60% dispersion in mineral oil, 539 mg, 21 mmol) at 0C under argon was added 4-bromo-1H-imidazole (3 g, 20 mmol) in one portion. The mixture was stirred for 5 min at 0C. A solution of 2-(trimethylsilyl)ethoxymethyl chloride (4.3 mL, 24 mmol) in DMF (3 mL) was added dropwise. Afterstirring at 0 C for 1 h, the mixture was warmed slowly to rt and stirred for 6 h. The mixture was then partitioned betweenEtOAc (100 mL) and water (50 mL). The EtOAc layer was separated and washed with brine, dried over Na2SO4, filtered,and the filtrate was concentrated under reduced pressure. The residue was purified via silica gel flash chromatography(eluting with a gradient of 100% hexanes to 100% EtOAc) to afford a regioisomeric mixture of 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole and 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole as an oil (2.9 g, 53%). Step 2: To a mixture of 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole and 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (345 mg, 1.3 mmol) from Step 1 of this Example, and 1-methylpyrazole-4-boronicacid pinacol ester (390 mg, 1.9 mmol) in DME (3 mL) was added K2CO3 (691, 5 mmol). Argon was bubbled into themixture for 5 min followed by the addition of Pd(PPh3)2Cl2 (44 mg, 0.06 mmol). Argon was bubbled into the mixture foran additional 5 min. Then the reaction vessel was sealed and the mixture was heated at 100 C for 15 h. The mixturewas cooled to rt, then partitioned between EtOAc (100 mL) and water (50 mL). The EtOAc layer was separated andwashed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified viasilica gel flash chromatography eluting with a gradient of 100% CH2Cl2 to 10% MeOH in CH2Cl2 to afford a regioisomericmixture of 1-methyl-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)-1H-pyrazole and 1-methyl-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)-1H-pyrazole as an oil (280 mg, 82%). LCMS (ESI) m/z 280 (M+H)+. Step 3: A mixture of 1-methyl-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)-1-pyrazole and 1-methyl-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)-1H-pyrazole (170 mg, 0.7 mmol) from Step 2 of this Examplewere stirred in a 1:1 mixture of TFA and CH2Cl2 (5 mL) for 15 h. The mixture was then concentrated under reducedpressure to afford 4-(1H-imidazol-4-yl)-1-methyl-1H-pyrazole (248 mg) as an oil and was used in the next step withoutfurther purification. LCMS (ESI) m/z 149 (M+H)+.

According to the analysis of related databases, 2302-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ambit Biosciences Corporation; HADD, Michael J.; HOCKER, Michael D.; HOLLADAY, Mark W.; LIU, Gang; ROWBOTTOM, Martin W.; XU, Shimin; (299 pag.)EP2766359; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33468-69-8, The chemical industry reduces the impact on the environment during synthesis 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, I believe this compound will play a more active role in future production and life.

a) To a vial was added 4-trifluoromethyl-1H-imidazole (953 mg, 7 mmol), 7 mL of ethanol, and sodium ethoxide (524 mg, 7.7 mmol). To this mixture was slowly added ethyl bromoacetate (1.29 g, 7.7 mmol). After 18 hours, an additional 100 muL of ethyl bromoacetate and approximately 100-200 mg of NaOEt were added. After 90 minutes, the reaction was quenched with NaHCO3 and extracted with 3¡ÁEtOAc. The organic layer was concentrated and the residue was purified by flash chromatography (SiO2, 80 g column, eluting with 15-90% EtOAc in hexanes) to provide 746 mg (48%) of the title compound as a crystalline solid. MS: (ES) m/z calculated for C8H10F3N2O2 [M+H]+ 223.1, found 223.1.

The chemical industry reduces the impact on the environment during synthesis 4-(Trifluoromethyl)-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ChemoCentryx, Inc.; Chen, Xi; Dragoli, Dean R.; Fan, Pingchen; Li, Yandong; Powers, Jay P.; Punna, Sreenivas; Tanaka, Hiroko; Zhang, Penglie; US2014/57937; (2014); A1;,
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Imidazole | C3H4N2 – PubChem

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. 71759-89-2 name is 5-Iodo-1H-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. 71759-89-2

After dissolving 4-iodo -1Himidazole(compound 1) (1.9g, 10mmol) in dichloromethane (40mL), under ice-cooling,triethylamine (2.1mL, 15mmol), trityl chloride (3.4g, 12mmol) It was added, under argon, andstirred for 17 hours at room temperature (25 C). After completion of the reaction, water wasadded, and the mixture was extracted twice with dichloromethane. The combineddichloromethane layers were dried anhydrous sodium sulfate and concentrated under reducedpressure, silica and the resulting crude product was gel column chromatography (eluent:chloroform / n-hexane = 1/1 ? chloroform) at Purification, Compound 2 It was obtained (4.1g,9.3mmol, 93% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Iodo-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Japan Medi-Physics Co., Ltd.; Kyoto University; Okumura, Yuki; Izawa, Akihiro; Akama, Kei; Kobashi, Shinya; Abe, Tsutomu; Saji, Hideo; Kimura, Hiroyuki; (20 pag.)JP2015/93833; (2015); A;,
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Imidazole | C3H4N2 – PubChem

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. 570-22-9 name is 1H-Imidazole-4,5-dicarboxylic acid, 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. 570-22-9

Example 29 Diethyl imidazole-4,5-dicarboxylate (46) Imidazole-4,5-dicarboxylic acid (7.55 g, 50.0 mmol) is dissolved in absolute ethyl alcohol (120 mL). The solution was cooled in an ice bath to 0 C. and bubbled dry HCl gas for 1 h. Later, the reaction mixture was refluxed at 80 C. for 7 h during which time all the starting material was consumed. The solvent was removed and the residue that obtained was dissolved in dichloromethane (200 mL) and the organic layer was neutralized with triethylamine. The organic layer was washed with cold water (100 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give 5.50 g (52%) of white solid: mp 175-177 C.; 1 H NMR (CDCl3) delta 1.40 (t, 3H), 4.41 (m, 2H), 7.84 (1H, C2 H) and 11.55 (br s, 1H, NH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4,5-dicarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; ICN Pharmaceuticals, Inc.; US6130326; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 3314-30-5 name is 1H-Benzo[d]imidazole-2-carbaldehyde, 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. 3314-30-5

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¡ãC, 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, 3-(2-aminoethyl)-N-benzylbenzamide hydrochloride (380) (171 mg, 0.59 mmol), 1 H-1 ,3-benzodiazole-5-carbaldehyde (129 mg, 0.88 mmol) and DIPEA (102 muIota, 0.59 mmol) in MeOH (5 ml) at room temperature for 72 h, followed by the addition NaB4 (33 mg, 0.88 mmol) gave the title compound (75 mg, 33percent) as a beige solid after purification by basic prepHPLC followed by trituration with DCM. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.16 (s, 1 H), 8.98 (t, J = 5.9 Hz, 1 H), 7.75 (s, 1 H), 7.73 – 7.69 (m, 1 H), 7.54 – 7.39 (m, 2H), 7.39 – 7.34 (m, 2H), 7.32 – 7.29 (m, 4H), 7.26 – 7.20 (m, 1 H), 7.15 – 7.07 (m, 2H), 4.47 (d, J = 6.0 Hz, 2H), 3.93 (s, 2H), 2.86 – 2.77 (m, 4H)

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

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

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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows., 6160-65-2

Amine (Intermediate A47,16 g, 0.0437 mol) was dissolved in pyridine (200 mL). To this solution was added 1,1′-thiocarbonyldiimidazole (11.68 g, 0.0. 655 mol) and stirred at room temperature overnight under argon. To the reaction mixture was added water (400 mL) and stirred for 1 hr. The resulting solid was collected, washed with water (600 mL) and dried to give 16.9 g (95%) of the title compound, benzimidazolethiol.

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; GARST, Michael, E.; SACHS, George; SHIN, Jai, Moo; WO2004/9583; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-89-2, The chemical industry reduces the impact on the environment during synthesis 71759-89-2, name is 5-Iodo-1H-imidazole, I believe this compound will play a more active role in future production and life.

To a solution of 4-iodoimidazole (50 g, 258 mmoles) in DMF (500 ml) was added triethyl amine (37.7 ml, 270.6 mmoles) and than triphenylmethyl chloride (69.7 g, 250 mmoles). After stirring at room temperature for 48 hours, the solution was poured into ice water (2.5 L). The solid was filtered and pumped on for several hours to yield the crude compound. Ethyl ether (200 ml) was added to the crude compound and the solution was filtered to yield 4-IODO-1-TRITYL-LH-IMIDAZOLE (104.1, 93%) as a white solid. ME (437)

The chemical industry reduces the impact on the environment during synthesis 5-Iodo-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHIRON CORPORATION; WO2004/96822; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem