Category: 20485-43-2

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. 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C5H6N2O2

Given that A’l4-mcthyl substituted tubulysins (such as A14-desacetoxytubulysin H, (Nicolaou, et al., 2016; Wipf & Wang, 2007) Tbl) have been proven more potent than their L’|4-H and A14-acetoxytubulysin (such as tubulysin H) coimterparts, considerable efforts were focused on designing and synthesizing a number of A’l4-mcthyl substituted tubulysins. Scheme 4 summarizes the synthesis of A’l4-mcthyl substituted tubulysins Tb50 and Tb51, in which the pipecolic acid residue of the molecule is replaced with pyrrole and A-Me substituted imidazole structural motifs, respectively. Thus, cleavage of the Fmoc protecting group from previously synthesized intermediate 22 through the action of | A’, A’-b i s(2-am i nocthy 1 )- 1.2- ethanediamine] followed by coupling of the so generated amine with 1 -methyl- lA-pyrrole-2 -carboxylic acid (23) and 1 -methyl- lA-imidazole-2-carboxy lie acid (24) provided Al4-dcsacctoxy tubulysin analogues Tb50 and Tb51, in 74% and 76% yields, respectively, as summarized in Scheme 4.

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

Related Products of 20485-43-2,Some common heterocyclic compound, 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, molecular formula is C5H6N2O2, 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: Reaction monitoring. To check the progress of the reaction, some resin beadswere taken, mixed with 30 muL of 95% TFA solution and shaken for a fewseconds, while the beads turn red. The supernatant solution was removed andmixed 1:1 with H2O. 1 muL of the aqueous solution was mixed with 1 muL of DHBmatrix on the target, dried and the mass spectrum was measured by MALDI-ToF-MS. If necessary, the deprotection was repeated.Fmoc deprotection. The amino protecting group Fmoc was cleaved after eachcoupling step to allow the coupling of the next amino acid. For this, the resinwas swollen in DMF and then suspended three times for 15 minutes in a 20%piperidine solution in DMF. The resin was filtered off and washed twice withCH2Cl2, DMF and again CH2Cl2.Coupling reactions. The resin was swollen in DMF. The amino acid (3 equiv)was dissolved in DMF containing DIPEA (9 equiv) and the coupling reagent(HBTU or PyBOP, 3 equiv) was added for pre-activation. After 5 minutes thesolution was added to the resin, and the suspension was mixed for 1.5 hours byshaking. The resin was then filtered off with suction and washed twice withCH2Cl2, DMF and again CH2Cl2. The completeness of the reaction was checkedwith MALDI-ToF-MS. If necessary, the coupling reaction was repeated.Cleavage from the resin. After swelling in CH2Cl2, the acid-labile 2 chlorotritylresin containing the polyamide was mixed with a 2.5% solution ofS7CH2Cl2/TFA/TIS 95:2.5:2.5 (v/v/v), mixed for 5 minutes and filtered off. This wasrepeated until the discoloration of the filtrate was complete. The combinedfiltrates were evaporated and the oily residue was treated with a mixtureH2O:MeCN and lyophilized.

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

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. 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 20485-43-2

To a stirred solution of 2- [5-(azetidin-3-ylamino)-pyridin-3-yl] -5-chloro-3,3-dimethyl-2,3- dihydro-isoindol-1-one (Example lEA], 56 mg, 0.163 mmol) and Et3N (0.5 mL) in DCM (5 mL) was added HATU (124 mg, 0.326 mmol) and 1-methylimidazole-2-carboxylic acid(27 mg, 0.2 12 mmol) at room temperature and stirring was continued at room temperature for 1 hour. The resulting reaction mixture was extracted with EtOAc (2 x 50 mL) and the combined organics were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product, which was purified by Prep-HPLC to afford title compound (15.4 mg, 21%) as a white foam. MS: 451.1 (M+Hj.

According to the analysis of related databases, 20485-43-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191340; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 20485-43-2,Some common heterocyclic compound, 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, molecular formula is C5H6N2O2, 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)Resin swelling: 400 mg of Fmoc-protected phenylhydrazine (0.66 mmol / g, 0.264 mmol) and 3 mL of CH2CI2 were added to a 10 mL solid phase reactor, the resin was swollen for 30 min, CH2CI2 was withdrawn, (b)Remove Fmoc protecting group: A solution of 3 mL of 20% piperidine / DMF was added to the swollen resin in step (a), N2 After bubbling, lOmin, the solvent was extracted, then 3 mL of 20% piperidine / DMF solution was added, N2 was bubbled and mixed. After lOmin, the resin was washed with DMF (4 x 3 mL) and the resin was washed with 3 mL of anhydrous DMF ,spare; (c) Amino acid condensation: A solution of 4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylic acid (254 mg, 1.056 mmol) and triphosgene (BTC, 128 mg, 0.433 mmol) in 2 mL of anhydrous THF was added to the solution Slowly dropwise trimethyl P-pyridine (Col 1 idine, 488yL, 3.696mmol), the reaction immediately produced a large number of white precipitate, added reaction 3min, (5%, nu / nu), the white precipitate was completely disappeared, and the reaction solution was transferred to the phenylhydrazine resin in which the protecting group was removed in step (b), N2 was bubbled and mixed, and the condensation reaction was 0.5 ~ Lh, the reaction solution was extracted, and the resin was washed with DMF (4 x 3 mL),(d)Removal of tert-butoxycarbonyl protecting group: Washed with CH2C12 (2 X 3 mL) Extraction of CH2C12, adding 3. OmLTFA / benzoic acid / Eta2Omicron (nu: nu: nu = 92: 5: 2.5) mixed solution removal step (b) The reaction was carried out for 2 min and the mixture was stirred for 2 min. After adding the solvent to 3. OmL TFA / phenol / H20 (nu: nu: nu = 92: 5: 2.5) for 20 min, the mixture was treated with CH2C12 (2 X 3 mL) and DMF (4 x 3 mL), and the resin was washed with 3 mL of anhydrous DMF,Repeating the above condensation and deprotection steps (c) and (d) Until the synthesis of the peptide supported on the phenylhydrazine resin as shown in formula (8).(e)Amino acid condensation: A solution of 4-tert-butoxycarbonylamino-1-methyl-1H-imidazole-2-carboxylic acid (254 mg, 1.056 mmol) and triphosgene (BTC, 128 mg, 0.433 mmol) in 2 mL of anhydrous THF was added to the solution (Col 1 idine, 488yL, 3.696 mmol) was slowly added and the reaction immediately resulted in a large amount of white precipitate. After the reaction was added for 3 min, (5%, nu / nu), the white precipitate completely disappeared, and the reaction solution was transferred to the phenylhydrazine resin in which the protecting group was removed in step (b), N2 was bubbled and mixed, and the condensation reaction was carried out for 0.5 to 11 hours , The reaction solution was extracted, and the resin was washed with DMF (4 X 3 mL), Repeat the above condensation and deprotection steps () and (d), Until the synthesis of the peptide supported on the phenylhydrazine resin as shown in formula (9) is completed;(G) Gamma-amino acid condensation: A solution of R-2- (9-fluorenylmethoxycarbonylamino) -4-tert-butoxycarbonylaminobutyric acid (465 mg, 1.056 mmol) And triphosgene (128 mg, 0.433 mmol) Dissolved in 2 mL of anhydrous THF, To this solution was slowly added dropwise trimethylpyridine (488yL, 3.696 mmol) The reaction immediately resulted in a large amount of white precipitate, added to the reaction lmin, added HOAt (144 mg, 1.056 mmol) Then add 2mL DIEA / DMF solution (5%, nu / nu), reaction 5min, The white precipitate completely disappeared, and the reaction solution was transferred to a linear peptide supported on the phenylhydrazine resin represented by the formula (9) (NH2-Im-Im-Py-Py-phenylhydrazine resin), N2 bubbling, the condensation reaction was carried out for 0.5 to 11 hours, the reaction solution was extracted, The resin was washed with DMF (4 X 3 mL) to give a peptide supported on the phenylhydrazine resin represented by the formula (10)H) repeating the condensation and deprotection guard step (d) and (C), wherein the load until the completion of the synthetic peptides to give formula (11) in a phenylhydrazine of the resin;I) repeating the condensation and deprotection guard step (d) and (E), wherein the load until the completion of peptide synthesis to give the formula (12) in the resin phenylhydrazineJ) Condensation of terminal amino acids: 1-methyl-1H-imidazole-2-carboxylic acid (132 mg, 1.56pimol) and PyBOP (550 mg, 1.056 mmo 1) was dissolved in 3 mL of anhydrous DMF, DIEA (350 yL, 2.112 mmol) was added, and the reaction was carried out for 5 min. The reaction solution was transferred to the reaction represented by the formula (12) obtained in step (h) (2), and the reaction was carried out for 2 hours. The reaction solution was purged with N2, and the resin was washed with DMF (4 X 3 mL), and the compound represented by the formula (12) was removed by the step (b) in Example 1 A Fmoc protecting group supported on a phenylhydrazine resin to obtain a peptide supported on the phenylhydrazine resin represented by the formula (13)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-2-carboxylic acid, its application will become more common.

Reference:
Patent; Shenzhen Advanced Technology Institute; Su Wu; Wang Wei; Pan Zhengyin; Cheng Zhehong; Wu Chunlei; Fang Lijing; (36 pag.)CN106674209; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 20485-43-2,Some common heterocyclic compound, 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, molecular formula is C5H6N2O2, 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.

Methyl 4- [ (TERT-BUTOXYCARBONYL) AMINO]-L-METHYLPYRROLE-2-CARBOXYLATE (0. 1108 g, 0.43 mmol) in 4 M HC1/ETOAC (4.26 ml) was stirred at room temperature for 30 min. The solvent was removed under reduced pressure and dried under vacuum for 1 hr. The residue was dissolved in DMF (4 ml) and ImCOOH (0.059 g, 0.52 mmol, 1. 2 equiv) was added followed by HOBt (0.079 g, 0.65 mmol, 1.5 equiv), TBTU (0.189 g, 0.65 mmol) and Et3N (0.328 ml, 2.6 mmol, 6 equiv) and the solution stirred for 1 hr. Solvent was removed and purified by flash chromatography (0-5 % MEOH/DCM).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-2-carboxylic acid, its application will become more common.

Reference:
Patent; UNIVERSITY OF WESTERN SYDNEY; WO2005/33077; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 20485-43-2, These common heterocyclic compound, 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, 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: : TBTU (0.90 g, 0.27 mmol) was added to a mixture of intermediate (G45) (0.1 g, 0.25 mmol) with 1 -methyl- lH-imidazole-2-carboxylic acid (0.40 g, 0.27 mmol) and DIEA (0.65 mL, 0.39 mmol) in DCM (5 mL). The reaction mixture was stirred at RT overnight. The reaction mixture was poured into water. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and evaporated till dryness. The residue was purified by column chromatography (silica gel, DCM). The pure fractions were collected and the solvent was evaporated to give 97 mg (76%) of compound (El).

Statistics shows that 1-Methyl-1H-imidazole-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 20485-43-2.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; LANCOIS, David, Francis, Alain; GUILLEMONT, Jerome, Emile, Georges; RABOISSON, Pierre, Jean-Marie, Bernard; ROYMANS, Dirk, Andre, Emmy; ROGOVOY, Boris; BICHKO, Vadim; LARDEAU, Delphine, Yvonne, Raymonde; MICHAUT, Antoine, Benjamin; (326 pag.)WO2016/174079; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 20485-43-2,Some common heterocyclic compound, 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, molecular formula is C5H6N2O2, 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 1-methyl-1H-imidazole-2-carboxylic acid (0.130 g,1mmol), EDC.HCl (0.29 g, 1.5mM), HOBt (0.20 g, 1.5mmol) and Et3N(0.15 g, 1.5 mM) in dichloromethane (10 mL) was stirred for 1 h at 0 C. Then, L-phenylalanine methyl ester.HCl (1.05 mM) was added into the solution. The reaction mixture was stirred for 12 h at 25 Cand then evaporated to dryness. The ester obtained was washed with water and extracted with dichloromethane (Scheme 1). To a solutionof the ester (1 equiv) in a dichloromethane/methanol (9:1 v/v)mixture, was added a methanolic solution of NaOH (3 equiv) withfinal concentration of the alkali being about 0.1-0.2 N. The reaction was monitored by TLC for the disappearance of starting ester. After the completion of the reaction, the solvents were removed under vacuum and the residue was diluted with water. Then, the aqueous phase was acidified to pH 2-3 with dilute HCl and extracted with ethyl acetate. The combined organic layers were dried with anhydrous sodium sulfate (Na2SO4) and the solvent was removed to afford the acid (PAIC). Single crystal of PAIC was isolated by slow evaporation of the solvent. Yield: 143 mg (74%), M.P- 129 C; Anal.Calc. for C14H15N3O3: C, 61.53; H, 5.53; N, 15.38. Found C, 61.13; H,5.45; N,15.18; 1H NMR (DMSO-d6, 400MHz): delta/ppm3.16 (d, J 4Hz,2H, CH2), 3.8 (s, 3H, NeCH3), 4.6 (m, H, chiral H), 6.9e7.2 (m, 7H,Aromatic H), 8.2 (d, J 8.4 Hz, 1H, amide-NH); 13C NMR: 34.9 (CH3),36.2 (eCH2), 52.9 (CeNH), 158.5 (COeN), 172(eCOO); FT-IR (KBr, cm-1)1555 (NeH), 1602 (eC]N), 3292 (HOeCO), 1673 (C]Oamide), 2931 (CeH); ESI mass: m/z 272.9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-2-carboxylic acid, its application will become more common.

Reference:
Article; Annaraj; Mitu; Neelakantan; Journal of Molecular Structure; vol. 1104; (2016); p. 1 – 6;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 20485-43-2, 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. 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 101-4; N- [3- ( {2- [ (cyclopropylcarbonyl) amino] [1,3] thiazolo [5, 4-b] pyridin- 5-yl } oxy) phenyl] -l-methyl-lH-imidazole-2-carboxamide; A mixture of N- [5- (3-aminophenoxy) [1, 3] thiazolo [5, 4- b]pyridin-2-yl] cyclopropanecarboxamide (175 mg, 0.536 mmol) , 1- methyl-lH-imidazole-2-carboxylic acid (101 mg, 0.804 mmol), HATU (367 mg, 0.965 mmol), N,N-diisopropylethylamine (420 muL, 2.41 mmol) and N,N-dimethylformamide (5 mL) was stirred at room temperature for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=50/50->0/100) and recrystallized from ethyl acetate-tetrahydrofuran to give the title compound (152 mg, 65%) as a white solid. 1H-NMR (DMSO-d6, 300 MHz) delta 0.94 – 1.01 (4H, m) , 1.95 – 2.04 (IH, m) , 3.97 (3H, s) , 6.86 – 6.91 (IH, m) , 7.07 – 7.15 (2H, m) , 7.38 (IH, t, J = 8.1 Hz), 7.44 (IH, d, J = 0.3 Hz), 7.67 – 7.74 (2H, m), 8.18 (IH, d, J = 9.0 Hz), 10.47 (IH, s) , 12.70 (IH, s) .

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-Methyl-1H-imidazole-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/150015; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, 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 20485-43-2, Formula: C5H6N2O2

A solution of the dipyrrole (50 mg, 0.138 mmol) resulting after coupling of the pyrrolicacid 10, as described in the previous experiment, in MeOH:DMF (4.5 mL : 0.7 mL) was hydrogenated for 1 h over 10% palladium on charcoal (30 mg). The catalyst was removed by filtration through celite and the filtrate concentrated. The residue was dissolved in DMF (1.0 mL), cooled to 0 C and added to a solution of acid 12 (13.4 mg,0.106 mmol), DECP (0.04 mL, 0.212 mmol), Et3N (0.13 mL, 0.903 mmol) and DMAP(catalytic) in THF (3.0 mL) at -10 C. The mixture was stirred for 15 h at -10 C. Thesolvents were removed under reduced pressure and the resulting residue purified by flash chromatography (aluminum oxide, 10% MeOH) to give 1b as a yellow-brownsolid (30.7 mg, 66%).

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:
Article; Jimenez-Balsa, Adrian; Dodero, Veronica I.; Mascarenas, Jose L.; Tetrahedron; vol. 69; 36; (2013); p. 7847 – 7853;,
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. 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