Tag: M.W=100-200

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. 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C5H6N2O2

Example 14[[3-(2′,4′-Difluoro-biphenyl-4-yloxymethyl)-benzyl]-(1-methyl-imidazole-2-carbonyl)-amino]-acetic acid; [3-(2′,4′-Difluoro-biphenyl-4-yloxymethyl)-benzylamino]-acetic acid ethyl ester (205 mg, 0.5 mmol) was mixed with N-methyl-imidazole-2-carboxylic acid (126 mg, 1.0 mmol) in DMF (6 mL). The mixture was stirred and BOP reagent (331.8 mg, 0.749 mmol), diisopropylethylamine (0.18 mL, 0.97 mmol) was added. The mixture was stirred at room temperature overnight and solvent was evaporated. The residue was extracted with ethyl acetate and saturated ammonium chloride solution. The organic layer was washed with water and concentrated sodium bicarbonate solution. Solvent was removed and the residue was purified through a flash column chromatography (ethyl acetate in hexanes 10% to 100%) to give [[3-(2′,4′-difluoro-biphenyl-4-yloxymethyl)-benzyl]-(1-methyl-imidazole-2-carbonyl)-amino]-acetic acid ethyl ester (237 mg, 91.5% yield).

The synthetic route of 20485-43-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bolin, David Robert; Hayden, Stuart; Qian, Yimin; Thakkar, Kshitij Chhabilbhai; US2011/136792; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, 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. name: 4-Amino-1H-benzo[d]imidazol-2(3H)-one

Preparation of 1-(4-chloro-2-(piperidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea Amine 2ah (1.34g, 6mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.78 g, lequiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 10 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (900 mg, 6 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 40 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 750 mg of a white solid. Yield = 31% 1HNMR (DMSO, 200 MHz) delta 1.58 (2H, m), 1.66 (4H, m), 2,78 (4H, M), 4.32 (2H, d, J = 6 Hz), 6.63 (1H, dd), 6.73 (1H, t), 6.94 (1H, t), 6.95 (1H, dd), 7.06 (2H, m), 7.29 (1H, d), 8.35 (1H, bs), 10.05 (1H, bs), 10.60 (1H, bs); [M+1] 400.2 (C20H22ClN5O2 requires 399.87)

The synthetic route of 75370-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmeste S.r.l.; EP2377850; (2011); 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 6160-65-2 as follows. Computed Properties of C7H6N4S

4-Aminobenzoic acid (5 mmol) was slowly added to a solution of TCDI (6 mmol) and TEA(5.5 mmol) in DCM (7.5 mL) at 0 C. The mixture was stirred for 2h at 0 C and then added dropwise to 4Maqueous HCl (9 mL). The precipitation was filtered and washed with 1M aqueous HCl (1mL2). Ther esulting sold was dried to aord 4-isothiocyanatobenzoic acid in yield of 90%. Methyl 2-cyanoacetate(2 mmol) followed by a solution of 4-isothiocyanatobenzoic acid (2 mmol) in anhydrous DMF (2 mL)were added to a cold suspension of powdered KOH (4 mmol) in dry DMF (2 mL). The mixture was stirred at room temperature for 0.5 h, then cooled again to 0 C, treated with a solution of 2-chloroacetylchloride (3 mmol) in anhydrous DMF (2 mL) and stirred at room temperature overnight. The mixturewas poured into ice-cold water, and the resulting precipitate was filtered o, dried, and crystallizedfrom DCM-EtOH to give intermediate IM in yield of 68%.

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:
Article; Zeng, Fanxun; Quan, Lina; Yang, Guantian; Qi, Tiantian; Zhang, Letian; Li, Shiliang; Li, Honglin; Zhu, Lili; Xu, Xiaoyong; Molecules; vol. 24; 15; (2019);,
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Imidazole | C3H4N2 – PubChem

Related Products of 71759-89-2, 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 71759-89-2 as follows.

Step 1.To a mixture of 13a (5 g, 0.026 mol) in DCM (100 mL) was added Et3N (3.9 g, 0.038 mol) and TsCI (5.87 g, 0.030 mol) at 0 C, and the mixture stirred at rt for 48 h. The reaction was poured into water (100 mL) and extracted with EtOAc (200 mL). The organic layer was dried with Na2S04 and concentrated under reduced pressure. The residue was purified by flash column to afford 14a (6.0 g, 66.8%).

According to the analysis of related databases, 71759-89-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYROS PHARMACEUTICALS, INC.; PARAZA PHARMA, INC.; CIBLAT, Stephane; DEROY, Patrick; LEBLANC, Melissa; MARINEAU, Jason, J.; MOORE, Joel; ROY, Stephanie; SIDDIQUI, M., Arshad; SPROTT, Kevin; WINTER, Dana, K.; KABRO, Anzheliika; LEGER, Serge; MILLER, Tom; SCHMIDT, Darby; BRADLEY, Michael; WO2015/58163; (2015); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17325-26-7, 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Methyl 1H-imidazole-4-carboxylate (500?mg, 3.96?mmol, 1.0 equiv.) was suspended in dry THF (30?mL). Sodium hydride (60% in mineral oil, 238?mg, 5.95?mmol, 1.5 equiv.) was added at 0?C. After 0.5?h of stirring, Hoffer’s chloro sugar (2.29?g, 5.95?mmol, 1.5 equiv.) was added in three portions over 1?h. The reaction mixture was stirred at ambient temperature overnight, and the solvent was removed in vacuo. The residue was dissolved in CH2Cl2 (100?mL) and washed with water (3?*?25?mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo. After purification by column chromatography (cyclohexane:ethyl acetate 2:1???ethyl acetate), compound 6 was obtained as a white solid (965?mg, 2.02?mmol, 51%). HRMS ESI m/z: [M?+?Na]+ 501.1649 (calcd. 501.1638). Elemental analysis (%): found: C 65.1, H 5.4, N 5.8; calcd. for C26H26N2O7: C 65.3, H 5.5, N 5.9. 1H NMR (400?MHz, CDCl3), delta/ppm: 7.94-7.90 (m, 2H, Tol), 7.89-7.85 (m, 2H, Tol), 7.76 (d, 1.4?Hz, 1H, H5), 7.70 (d, 1.4?Hz, 1H, H2), 7.28-7.21 (m, 4H, Tol), 6.13 (dd, 8.1?Hz, 5.6?Hz, 1H, H1′), 5.65 (dt, 6.1?Hz, 2.4?Hz, 1H, H3′), 4.62 (d, 3.7?Hz, 2H, H5′, H5″), 4.58 (td, 3.7?Hz, 2.4?Hz, 1H, H4′), 3.83 (s, 3H, OCH3), 2.75 (ddd, 14.2?Hz, 5.7?Hz, 2.4?Hz, 1H, H2′), 2.64 (ddd, 14.2?Hz, 8.1?Hz, 6.2?Hz, 1H, H2″), 2.42 (s, 3H, CH3), 2.40 (s, 3H, CH3). 13C NMR (101?MHz, CDCl3), delta/ppm: 166.1 (C=O (Tol)), 165.8 (C=O (Tol)), 162.8 (C=O), 144.6 (Tol), 144.2 (Tol), 136.2 (C2), 134.4 (C4), 129.7 (Tol), 129.6 (Tol), 129.3 (Tol), 129.3 (Tol), 126.5 (Tol), 126.2 (Tol), 122.5 (C5), 86.6 (C1′), 83.1 (C4′), 74.8 (C3′), 63.8 (C5′), 51.6 (OCH3), 39.6 (C2′), 21.7 (CH3), 21.6 (CH3).

The synthetic route of Methyl 1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sandmann, Nikolas; Defayay, Denise; Hepp, Alexander; Mueller, Jens; Journal of Inorganic Biochemistry; vol. 191; (2019); p. 85 – 93;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 15965-31-8,Some common heterocyclic compound, 15965-31-8, name is 5-Chloro-1H-imidazole, molecular formula is C3H3ClN2, 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 27: Methyl {2-[(5-chloro-1 H-imidazol-1-yl)methyl1phenyl)acetateMethyl [2-(bromomethyl)phenyl]acetate (Intermediate 1 , 3 g, 12.34 mmol) and 4-chloro- 1 H-imidazole (Intermediate 26, 3.80 g, 37.0 mmol) were dissolved in dry DMF (100 ml) and stirred at room temperature for 16 hours. After dilution with water the mixture was extracted with DCM, the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (5Og) eluting with a gradient of MeOH in DCM from 0 to 5% to afford the title compound (1.6 g, 6.04 mmol) contaminated with -10% of the regioisomer methyl {2-[(4-chloro-1 H-imidazol- 1-yl)methyl]phenyl}acetate, which was used in the next step without further purification; UPLC/MS Rt=0.50 min; m/z (ES): 265 and 267 [M+H]+ ; 1H NMR (CDCI3) only signals relating to the title compound: delta 3.71 (s, 2H), 3.72 (s, 3H), 5.21 (s, 2H), 6.92 (d, 1 H), 7.05 (d, 1 H), 7.28-7.42 (m, 4H).

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

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; GIANOTTI, Massimo; LESLIE, Colin Philip; STASI, Luigi Piero; WO2010/142652; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1848-84-6, These common heterocyclic compound, 1848-84-6, name is 2-Ethyl-1H-benzo[d]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.

A mixture of 2- { 1 -[2-chloro-9-methyl-6-((5)-3-methylmorpholin-4-yl)-9H- purin-8-ylmethyl]piperidin-4-yl}propan-2-ol (200 mg, 0.47 mmol), 2-ethylbenzimidazole (73 mg, 0.50 mmol), tris(dibenzylideneacetone)dipalladium (12 mg, 2.5 molpercent), XPhos (20 mg, 10 molpercent) and Cs2CO3 (218 mg, 0.67 mmol) in DMF (6 mL) was purged with argon then heated at 150 0C for 1 h in a microwave reactor. The reaction mixture was loaded onto an Isolute.(R). SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NEta3/MeOEta. The resulting residue was purified by column chromatography (Si-PCC, MeOH:DCM, 0-5percent) then (Si-PCC, MeOH:DCM, 0-3percent) affording 775 (95 mg, 38percent). LCMS (method I): Rx 2.65 min, [M+H]+ 533.3. 1H NMR (CDCl3, 400 MHz): delta 8.03-8.02 (1 H, m), 7.75-7.74 (1 H, m), 7.27-7.24 (2 H, m), 5.40 (2 H, brd s), 4.09-4.03 (1 H, m), 3.88 (3 H, s), 3.83 (2 H, s), 3.75-3.55 (4 H, m), 3.36 (2 H, q, J = 7.48 Hz), 2.98-2.95 (2 H, m), 2.11 (2 H, t, J = 10.92 Hz), 1.81-1.71 (2 H, m), 1.45-1.44 (6 H, m), 1.34-1.31 (4 H, m), 1.19 (6 H, s)

Statistics shows that 2-Ethyl-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 1848-84-6.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CASTANEDO, Georgette; CHAN, Bryan; GOLDSTEIN, David Michael; KONDRU, Rama K.; LUCAS, Matthew C.; PALMER, Wylie Solang; PRICE, Stephen; SAFINA, Brian; SAVY, Pascal Pierre Alexandre; SEWARD, Eileen Mary; SUTHERLIN, Daniel P.; SWEENEY, Zachary Kevin; WO2010/138589; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 401567-00-8, 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. 401567-00-8 name is 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, 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.

4.1.27. 5-Aminomethyl-2-(4-isopropoxyphenoxy)-1-((2-(trime-thylsilyl)ethoxy)methyl)benzimidazole and 6-aminomethyl-2-(4-isopropoxyphenoxy)-1-((2-(trimethylsilyl)ethoxy)methyl)benzimidazole (24)To a solution of 18 (0.21 g, 0.50 mmol) in 25% aq NH3 (1.6 mL)and EtOH (16 mL) was added Raney Ni (1.6 mL, in water). The mix-ture was stirred for 4 h under a hydrogen atmosphere, then lteredthrough a Celite pad, and the ltrate was concentrated underreduced pressure. The residue was puried by silica gel columnchromatography (CHCl3/MeOH = 8:1) to afford the product 24(0.20 g, 97%, 1:1 regioisomeric mixture) as a yellow oil.1H NMR (500 MHz, CDCl3) d 7.51 (s, 1/2H), 7.48 (d, J = 8.6 Hz,1/2H), 7.43 (s, 1/2H), 7.31 (d, J = 8.0 Hz, 1/2H), 7.24-7.20 (m, 2H),7.19-7.14 (m, 1H), 6.95-6.90 (m, 2H), 5.50 (s, 1H), 5.46 (s, 1H),4.55-4.48 (m, 1H), 3.97 (s, 1H), 3.92 (s, 1H), 3.64 (t, J = 8.3 Hz,1H), 3.63 (t, J = 8.0 Hz, 1H), 1.34 (d, J = 6.0 Hz, 3H), 1.34 (d,J = 6.0 Hz, 3H), 0.93 (t, J = 8.0 Hz, 2H), 0.04 (s, 9/2H), 0.05 (s,9/2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Okazaki, Shogo; Noguchi-Yachide, Tomomi; Sakai, Taki; Ishikawa, Minoru; Makishima, Makoto; Hashimoto, Yuichi; Yamaguchi, Takao; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5258 – 5269;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 21252-69-7,Some common heterocyclic compound, 21252-69-7, name is 1-Octyl-1H-imidazole, molecular formula is C11H20N2, 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.

Silver(I)-N-octylimidazole complexes were alsosynthesized using a previously reported method with a minor modification. Typically, N-octylimidazole (2 mol equiv.) was added to a solution of AgNO3 (1 mol equiv.) in ethanol (15 mE) and the reaction mixture was stirred at room temperature for 24 h. The reaction mixture was filtered and evaporation of the solvent mixture gave a brown oil or cream solid. The brown oil was re-dissolved in dichloromethane and extracted three times with watet The organic phase was dried on anhydrous sodium sulfate and the solvent was removed under reduced pressure. Other silver(I)-N-alkylimidazole complexes were synthesized in the same manner. The solid complexes were further purified by recrystallization by dissolving in dichloromethane and precipitated with hexane.

The synthetic route of 21252-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kleyi, Phumelele; Maity, Arjun; Ray, Suprakas Sinha; (16 pag.)US2018/255777; (2018); 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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Methyl-1H-imidazole-4-sulfonyl chloride

The production of compound No. 26 proceeds according to the sequence of reaction steps shown in the following schemes: The first sub-step shown above was performed at 20 C. during 2 hours with a molar excess of CH2N2 (about 2 molar equivalents) in dry ether, then in a second sub-step (shown below) performed at 5 C. HCl gas was bubbled into the reaction mixture for 15 minutes, and the desired intermediate was obtained in 71% yield. For the conversion from 3 to 4, the first sub-step shown above was performed at 20 C. during 1 hour with a molar excess of thio-carbonyldiimidazole (about 2 molar equivalents) in THF, then in a second sub-step performed at 20 C. for 12 hours a 25% aqueous NH3 solution was added, and the desired intermediate was obtained in 72% yield. The conversion from 4 to 5 was performed during 6 hours with 1 molar equivalent NaHCO3 at reflux in methanol, and the desired intermediate was obtained in 92% yield. The conversion from 5 to 6 was performed during 3 hours at 20 C., and the desired intermediate was obtained in 90% yield. The conversion from 6 to the final compound was performed during 6 hours at 20 C. in 1,2-dichloroethane (DCE) in the presence of a molar excess of triethylamine (1.2 molar equivalents).

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NV reMYND; US2010/197703; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem