Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 7189-69-7, name is 1,1′-Sulfonyldiimidazole, 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 7189-69-7, name: 1,1′-Sulfonyldiimidazole

NaH (60% in oil, 0.070g, 1.76mmol) was added to a stirred solution of compound 13 (0.23g, 0.16mmol) in dry DMF (3.5mL) at room temperature. After 1h, the suspension was cooled at -40C and 1,1?-sulfonyl-diimidazole (0.22g, 1.12mmol) in dry DMF (1.5mL) was added. After 24h the reaction mixture was quenched with MeOH and allowed to warm to room temperature, then diluted with water (40mL). The mixture was extracted with AcOEt (3×50mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. Flash chromatography (hexane/AcOEt, 7:3) of the crude product gave trisaccharide 14 (0.21g, 85%) as an amorphous solid. [alpha]D20=+1.8 (c=1 in chloroform). 1H NMR (CDCl3): delta=7.94 (br s, 1H, Im), 7.53-7.10 (m, 45H, arom), 7.00 (m, 2H, Im), 5.46 (s, 1H, PhCH), 5.25-5.12 (m, 3H, H-1? and CH2Ph), 4.97 (d, 1H, J=11.1Hz, CH2Ph), 4.85-4.58 (m, 10H, H-1 and CH2Ph), 4.58-4.44 (m, 4H, H-2? and CH2Ph), 4.32 (d, 1H, J1?,2?=7.9Hz, H-1?), 4.23 (dd, 1H, J5?,6?=4.9Hz, J6a?,6b?=10.6Hz, H-6a?), 4.16-4.09 (m, 1H, CH2Ph), 4.09-3.80 (m, 5H, H-2, 3, 3?, 4?, 5?), 3.75-3.52 (m, 5H, H-a, 4, 5, 2?,4?), 3.52-3.20 (m, 7H, H-a?, c, c?, 6a?, 6b?, 3?, 6b?), 3.10-2.98 (m, 1H, H-5?), 1.91-1.69 (m, 2H, 2H-b), 1.29-1.21 (br d, 3H, 3H-6). 13C NMR (CDCl3): delta=155.6 (C=O), 139.1-136.5 (9C, arom), 136.8 (C Im),129.2-126.0 (46C, arom.), 118.6 (C Im), 101.4 (CHPh), 98.6 (C-1?), 98.2 (C-1), 97.1 (br s, C-1?), 85.7 (C-2?), 81.9 (C-4?), 80.3 (br s, C-4), 79.5 (C-3?), 79.2 (C-2?), 78.4 (br s, C-3), 76.7 (C-3?), 76.5 (br s, C-2), 76.2 (C-4?), 75.2 (2C, CH2Ph), 74.6 (br s, CH2Ph), 74.3 (CH2Ph), 73.6 (CH2Ph), 73.1 (br s, CH2Ph), 70.2 (C-5?), 68.4 (C-6?), 68.3 (C-5), 67.3 (C-6?), 67.2 (CH2Ph), 65.7 (C-5?), 65.2 (C-a), 50.8 and 50.5 (NCH2Ph), 44.6 and 43.7 (C-c), 28.4 and 27.9 (C-b), 18.0 (C-6). MS (ESI) m/z (%): 1550.3 (100) [M+NaM+Na]+. HRMS (ESI): m/z calcd for C88H93N3O19NaS 1550.6022 [M+Na]+, found 1550.6055

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, 1,1′-Sulfonyldiimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Morelli, Laura; Fallarini, Silvia; Lombardi, Grazia; Colombo, Cinzia; Lay, Luigi; Compostella, Federica; Bioorganic and Medicinal Chemistry; vol. 26; 21; (2018); p. 5682 – 5690;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 68282-47-3, name is 2-Phenyl-1H-imidazole-4-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 68282-47-3, Computed Properties of C10H8N2O

Reference Example 14 1-[(2,6-difluorophenyl)sulfonyl]-2-phenyl-1H-imidazole-4-carbaldehyde To a solution of 2-phenyl-1H-imidazole-4-carbaldehyde (1.00 g) in tetrahydrofuran (70 mL) was added sodium hydride (60% in oil, 348 mg) at room temperature, and the mixture was stirred for 30 min. 2,6-Difluorobenzenesulfonyl chloride (1.36 g) was added to the reaction mixture, and the mixture was stirred for 1.5 hr. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from diethyl ether to give the title compound as colorless crystals (yield 1.36 g, 67%). 1H-NMR (CDCl3) delta: 6.82-6.91 (2H, m), 7.27-7.46 (5H, m), 7.51-7.60 (1H, m), 8.38 (1H, s), 9.98 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Phenyl-1H-imidazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2005957; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 53439-88-6, These common heterocyclic compound, 53439-88-6, name is 5-Amino-1,3-dimethyl-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.

To a 0 C. solution of 5-amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one (4 g, 22.6 mmol) in 25 mL of CHCl3 and 25 mL of AcOH was slowly added dropwise bromine (3.5 g, 22.6 mmol). The mixture was stirred at RT for 30 min, then concentrated and purified by silica gel chromatography (1:1 EtOAc/hexanes) to afford 5-amino-6-bromo-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one as a yellow solid (3.2 g, 69%). MS (ES+) C9H10BrN3O requires: 256. found: 257 [M+H]+.

The synthetic route of 53439-88-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Board of Regents, The University of Texas System; Palmer, Wylie; Jones, Philip; Liu, Gang; Petrocchi, Alessia; Reyna, Naphtali; Subrumanian, Govindan; Theroff, Jay; Yau, Anne; (114 pag.)US2016/60260; (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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

156.3 mg of the compound obtained in Synthesis Example 29-2 was dissolved in 2 ml of methanol, and then 2 ml of a 4 mol/l hydrochloric acid/dioxane was added to the solution, followed by stirring for 165 minutes at room temperature. On completion of the reaction, the solvent was distilled off. Subsequently, it was dissolved in 4 ml of anhydrous methanol, and then 131.1 mul of triethylamine and 62.8 mg of 1-methyl-2-formylbenzimidazole were added to the solution and the whole was stirred for 12 hours at room temperature. After the solvent was distilled off, subsequently, 4 ml of anhydrous methanol was added thereto and the whole was cooled to 0°C. Then, 19.8 mg of sodium borohydride was added to the solution and the whole was stirred for 30 minutes while being gradually returned to room temperature. On completion of the reaction, the solvent was distilled off and the residue was purified by means of silica gel column chromatography (10 g, chloroform/methanol = 10/1). After the resultant compound was dissolved in 2 ml of a 1 mol/l hydrochloric acid, water was distilled off. Consequently, 44.1mg of hydrochloride of the above-mentioned compound was obtained as a white-red solid product. MS(FAB,Pos.):m/z=642[M+1]+1H-NMR(500MHz,DMSO-d6):delta=1.73-1.91(4H,m),2.09(2H,br),3.64(3H,s ),3.85(3H,s),4.08-4.12(2H,m),4.38-4.43(2H,m),4.47-4.59(3H,m), 4.76-4.77(2H,m),5.98-5.99(1H,m),6.22-6.23(1H,m),6.79-6.80(1H, m),7.29-7.59(6H,m),7.60-7.73(2H,m),7.84-7.86(1H,m),7.94-8.08 (4H,m), 8.70-8.72 (2H,m), 8.96 (2H,br).

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 3012-80-4.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1389460; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 51605-32-4, These common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, 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.

Lithium hexamethyldisilazide (iM in tetrahydrofuran, 2i.4 ml, 2i.4 mmol) was added dropwise over iS mm to a stirred, cooled (-iO C) suspension of ethyl 4-methyl-i H25 imidazole-S-carboxylate (3.00 g, i9.S mmol) in dry dimethylformamide (200 ml) underan atmosphere of argon. After stirring for a further iO mi 0- (diphenylphosphoryl)hydroxylamine (5.45 g, 23.4 mmol) was added and the mixture was warmed to room temperature. After 6 h, water was added until a clearhomogeneous solution formed and subsequently the mixture was evaporated todryness. The resultant solid was treated with dichloromethane and the mixture wasfiltered and the filter cake was washed with further portions of dichloromethane. Thecombined filtrate and washings were evaporated to give a solid which was purified byflash chromatography (methanol-dichloromethane gradient, 0:100 rising to 5:95) togive 1.75 g (10.3 mmol, 53% yield) of the title compound as a white solid. Purity 100%.1H NMR (300 MHz, Chloroform-d) ppm 7.59 (s, 1H), 5.33 (br s, 2H), 4.37 (q, 2H, J =7.4 Hz), 2.46 (s, 3H), 1.40 (t, 3H, J = 7.4 Hz).UPLC/MS (3 mm) retention time 0.56 mm.LRMS: m/z 170 (M+1).

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; AIGUADE BOSCH, Jose; CONNOLLY, Stephen; EASTWOOD, Paul Robert; GOMEZ CASTILLO, Elena; MORENO MOLLO, Immaculada Montserrat; ROBERTS, Richard Spurring; SEVILLA GOMEZ, Sara; (216 pag.)WO2017/60488; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 32673-41-9, 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 32673-41-9 as follows.

Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid.

According to the analysis of related databases, 32673-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dinsmore, Christopher J.; Bergman, Jeffrey M.; US2002/10184; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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.

Intermediate le 5-Iodo- l-(2,2,2-trifluoroethyl)- lH-imidazole In a 50 mL three-necked flask, 4-iodo-lH-imidazole (0.500 g, 2.58 mmol, Eq: 1.00) was combined under Ar with THF (7 ml) to give a colorless solution. Sodium hydride 55% (337 mg, 7.73 mmol, Eq: 3) was added at 0C (exothermic reaction, temperature rose to 17C). The reaction mixture was stirred at RT for 30 min. and then cooled down again to 0C, before 2,2,2-trifluoroethyl trifluoromethanesulfonate (1.2 g, 5.16 mmol, Eq: 2), dissolved in THF (3 ml), was added. The white suspension was stirred at RT for additional 1.5 hours when TLC indicated that the reaction was complete. Work up: The reaction mixture was poured into 10 mL H20 and extracted with EtOAc (2 x 15 mL). The organic layers were combined, washed with brine, dried over Na2S04, and concentrated i. V. Purification : The crude product was purified by flash chromatography (silica gel, 70 g, 0% to 60% EtOAc in heptane) to yield 80 mg of the desired title compound as off-white solid, besides 619 mg of the unwanted 4-iodo-l-(2,2,2-trifluoro-ethyl)-lH-imidazole. MS (ESI): 276.9 [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:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; HORNSPERGER, Benoit; KUHN, Bernd; MAERKI, Hans, P.; MAYWEG, Alexander, V.; MOHR, Peter; TAN, Xuefei; WO2013/120771; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, 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 6160-65-2, Computed Properties of C7H6N4S

[00241] A solution of the amine (0.110 g, 0.43 mmol) in anhydrous CH2CI2 (2 ml_) was added dropwise over 2-5 minutes to an ice-salt bath cooled solution of 1 , 1′-thiocarbonyldiimidazole (95%, 0.162 g, 0.87 mmol, 2 eq.) in anhydrous CH2CI2 (6 ml_). After 15 minutes, the cooling bath was removed and the reaction mixture was stirred at room temperature for 1.5 hours after which time analysis by TLC (10% MeOH in CH2CI2) indicated complete consumption of the starting aniline. The mixture was cooled once again in an ice bath and 7 M NH3 in MeOH (620 mu, 4.3 mmol, 10 eq.) was added dropwise over 2-5 minutes. The bath was removed and the mixture was stirred over night at room temperature. Silica gel (~1 g) was added and the mixture was concentrated to dryness under reduce pressure. Flash column chromatography (RediSepRf Si02 (40 g), 100% CH2CI2? 10% MeOH in CH2CI2) gave the thiourea as an amber oil that solidified upon standing (0.130 g, 97%).

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, 1,1′-Thiocarbonyldiimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DUKE UNIVERSITY; LIEDTKE, Wolfgang; (189 pag.)WO2017/177200; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 872-82-2,Some common heterocyclic compound, 872-82-2, name is 2-(1H-Imidazol-5-yl)ethanol, molecular formula is C5H8N2O, 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 imidazole derivatives (4a-c, 10mmol), 4-amino-6-chloropyrimidine (1.30g, 10mmol), and K2CO3 (2.07g, 15mmol, for 5a) or Cs2CO3 (3.91g, 12mmol, for 5b-c) was stirred in DMF (20mL) at 100C (for 5a) or at 140C (for 5b-c) for 12h. Water (100mL) was then added. The mixture was extracted with EtOAc (3×50mL). The organic layer was separated and dried over Na2SO4. Removal of the solvents produced a residue which was purified using column chromatography and eluted with a mixture of MeOH:CH2Cl2 (1:30, v:v) to afford 5a-c.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1H-Imidazol-5-yl)ethanol, its application will become more common.

Reference:
Article; Xu, Yi-xiang; Wang, Huan; Li, Xiao-kang; Dong, Sheng-nan; Liu, Wen-wen; Gong, Qi; Wang, Tian-duan-yi; Tang, Yun; Zhu, Jin; Li, Jian; Zhang, Hai-yan; Mao, Fei; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 33 – 47;,
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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C5H6N2O

lb lb. 3-({4-[(2-Hydroxyethyl)(methyl)carbamoyl]phenyl}({l-[(4-methyl-lH-imidazol-5-yl)methyl]piperidin-4-ylidene})methyl)benzamide 3-({4-[(2-Hydroxyethyl)(methyl)carbam benzamide (79.0 mg, 0.2 mmol) was dissolved in 1 ,2-dichloroethane (2 mL) and acetic acid (57 muIota_, 1 .0 mmol) was added followed by 5-methylimidazole-4-carboxaldehyde (44.0 mg, 0.4 mmol) and NaBH(OAc)3 (169 mg, 0.8 mmol). The reaction was stirred at 50C for 48 h. The crude was purified by flash chromatography (ethyl acetate, ethyl acetate/methanol 75:25) to give the title compound as a crude material. This material was then purified by preparative HPLC (X-bridge column, 50 mM NH4HCO3 as mobile phase, CH3CN from 10 to 40) to give 5 mg of the title compound. MS m/z 488 [M+H]+.

The synthetic route of 68282-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMNOVO AB; VON MENTZER, Bengt; STARKE, Ingemar; BRANDT, Peter; (24 pag.)WO2016/99394; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem