Category: 26663-77-4

Reference of 26663-77-4,Some common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-carboxylate, molecular formula is C9H8N2O2, 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.

REFERENCE EXAMPLE 8 (+)-4,5,6,7-tetrahydrohenzimidazole-5-carboxylic acid hydrochloride Methyl benzimidazole-5-carboxylate was subjected to catalytic reduction according to the method described in CROATICA CHEMICA ACTA 45, 297-312 (1973), to obtain methyl 4,5,6,7-tetrahydrobenzimidazole-5-carboxylate.

The synthetic route of 26663-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tokyo Tanabe Company Limited; US5677326; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 26663-77-4, name is Methyl benzimidazole-5-carboxylate, 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 26663-77-4, category: imidazoles-derivatives

8.2. PREPARATION OF 3,4-DIISOTHIOCYANATOBENZOIC ACID, METHYL ESTER, 11 A 250 ml round bottom flask was charged with 4.98 g (50 mmol) of calcium carbonate, 10 ml of methylene chloride, and 3 ml of water. The resultant slurry was cooled to 10 C. and then 2.27 ml (3.43 g, 30 mmol) of thiophosgene (Aldrich) followed by 2.50 g (14.2 mmol) of 5-benzimidazolecarboxylic acid, methyl ester, 10, dissolved in 50 ml of a 1:1 mixture of acetonitrile in water were slowly added. The reaction mixture was stirred for 4 h and the temperature was allowed to rise to 15-20 C. The orange-white reaction slurry was then filtered and the filtrate was washed with three 50 ml portions of methylene chloride. The organic layers were combined, dried over MgSO4, filtered, and the solvents were removed under vacuum to leave a beige residue. This residue was triturated four times with petroleum ether to leave, after drying for 16 h at 25 C. at 30 mm pressure, 2.14 g (8.56 mmol, 60% yield) of 3,4-diisothiocyanatobenzoic acid, methyl ester, 11, as an off-white powder. 1 H NMR (CDCl3, TMS): delta7.85-7.95 (m, 2H), 7.30 (d, 1H), 3.92 (s, 3H). IR showed a doublet (NCS) at 2140 cm-1.

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, Methyl benzimidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cytogen Corporation; US5585468; (1996); A;,
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. 26663-77-4, name is Methyl benzimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C9H8N2O2

Compound 15 (0.5 g, 2.84 mmol) was reacted with 4-phenylbutylbromide (0.5 mL, 2.84 mmol) in anhydrous DMF(10 mL) and K2CO3 (0.79 g, 5.68 mmol) was added slowly at 0C.The resulting reaction mixture was warmed to 60C and stirredfor 2 h. After completion, reaction mixture was quenched withsaturated NH4Cl, and extracted with ethyl acetate (250 mL). Thecombined organic layers were washed with brine, dried overanhydrous Na2SO4, and concentrated in vacuo. The crude residuewas purified over silica gel column chromatography (MeOH/DCM= 1:49) to yield the mixture of isomers 16 (0.79 g, 90%) as acolorless liquid.Spectral data for isomers. 1H NMR (CDCl3, 300 MHz); delta8.53 (s, 1H), 8.10 (t, 2H, J= 6.0 Hz), 7.34-7.29 (m, 3H), 7.16-7.14(m, 3H), 4.23-3.94 (m, 2H), 2.68-2.63 (m, 2H), 2.30-2.20 (m, 2H).13C NMR (CDCl3, 75 MHz): 167.7, 147.3, 144.6, 139.9, 133.4,128.7, 126.5, 124.8, 123.5, 122.8, 120.1, 112.1, 52.2, 44.5, 32.6,30.9.

The synthetic route of 26663-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Srinivasrao, Ganipisetti; Park, Jung-Eun; Kim, Sungmin; Ahn, Mija; Cheong, Chaejoon; Nam, Ky-Youb; Gunasekaran, Pethaiah; Hwang, Eunha; Kim, Nam-Hyung; Shin, Song Yub; Lee, Kyung S.; Ryu, Eunkyung; Bang, Jeong Kyu; PLoS ONE; vol. 9; 9; (2014);,
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. 26663-77-4, name is Methyl benzimidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl benzimidazole-5-carboxylate

To a solution of methyl 1H-benzo[d]imidazole-5-carboxylate (0.90 g, 5.1 mmol) in DMF(20 ml) was added NaH (0.25 g, 6.2 mmol), and the reaction mixture was stirred at room temperature for 30 mm. Then (2-(chloromethoxy)ethyl)trimethylsilane (0.94 g, 5.6 mmol) wasadded and the reaction mixture was stirred at room temperature for 2 hours. When LCMS showed that the reaction completed, the reaction mixture was diluted with EtOAc (100 mL), washed with H20 (100 mL x 2) and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford crude product as an oil, which was purified by column chromatography on silica gel (eluted with petroleum ether/EtOAc = 1:1) to afford mixture ofmethyl 1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazole-5-carboxylate and methyl 1- ((2-(trimethylsilyl)ethoxy) methyl)- 1 H-benzo [d] imidazole-6-carboxylate as an oil. LC/MS (m/z): 307 (M+H).To a solution of LiA1H4 (0.30 g, 7.8 mmol) in THF (20 ml) was added solution of Step A product (1.2 g, 3.9 mmol) in THF (30 mL) at 0C, the reaction mixture was allowed to warm to room temperature and stirred for 3 hours. When TLC showed that the reaction completed, the reaction mixture was quenched with sat. aq. NH4C1 (50 mL) and the mixture was filteredthrough a pad of celite. The filtrate was extracted with EtOAc (100 mL), washed with H20 (100 mL) and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford mixture of (1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo [d] imidazol-5-yl) methanol and (1- ((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-6-yl)methanol as an oil, which was used in next step without further purification. ?H NMR (CDC13, 400 MHz) oe 8.03 (s, 1H), 8.02(s, 1H), 7.86-7.79 (m, 2H), 7.64 (s, 1H), 7.61-7.55 (m, 1H), 7.43 (d, J= 7.3 Hz, 1H), 7.36 (d, J=8.4 Hz, 1H), 5.59 (s, 4H), 4.90 (s, 2H), 4.87 (s, 2H), 3.59-3.53 (m, 4H), 0.99-0.91 (m, 4H), 0.00 (s, 9H).To a solution of Step B product (0.3 g, 1.1 mmol) in DCM(10 ml) was added SOC12 (0.8 ml, 10.8 mmol) dropwise at 0C, then the reaction mixture was stirred at room temperature for 3 hours. When TLC showed that the reaction completed, the reaction mixture was diluted with DCM (50 mL), washed with sat. aq. NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to afford a mixture of 5-(chloromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d] imidazole and 6-(chloromethyl)- 1 -((2- (trimethylsilyl) ethoxy)methyl)-1H-benzo[d]imidazole as an oil, which was used in next step without further purification. LC/MS (m/z): 297 (M+H).

According to the analysis of related databases, 26663-77-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; CAI, Jiaqiang; CRESPO, Alejandro; DU, Xiaoxing; DUBOIS, Byron Gabriel; LIU, Ping; LIU, Rongqiang; QUAN, Weiguo; SINZ, Christopher; WANG, Liping; (61 pag.)WO2016/49100; (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. 26663-77-4, name is Methyl benzimidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 26663-77-4

A solution of methyl lH-benzo[d]imidazole-6-carboxylate (9.5 g, 53.9 mmol) in THF (100 mL) had NaH (2.59 g, 64.7 mmol) added at 0C. After stirring for 30 min, CH3I (13.23 g, 93.2 mmol) was added and the mixture was stirred at room temperature for lh. The reaction was then quenched by addition of water and extracted with DCM (3×100 mL). The combined organic layers were dried over Na2S04 and concentrated to give a mixture of two isomeric products methyl 1 -methyl- lH-benzo[d]imidazole-6-carboxylate and methyl 1- methyl-lH-benzo[d]imidazole-5-carboxylate (8.0 g, Yield 78%). LCMS (m/z): 191.06 (M+l). This crude mixture was used directly in the next step.

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 26663-77-4.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; MUNCHHOF, Michael, John; JIN, Lei; WO2014/100695; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 26663-77-4,Some common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-carboxylate, molecular formula is C9H8N2O2, 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.

Preparation Example 6 To a solution ofmethyl 1H-benzimidazole-5-carboxylate (8.5 g) in THF (85 ml) were added 3,4-dihydro-2H-pyran (5.3 ml) and (1S)-(+)-10-camphorsulfonic acid (1.1 g), followed by heating and refluxing for 24 hours. To the mixed reaction liquid were added 3,4-dihydro-2H-pyran (4.4 ml) and (1S)-(+)-10-camphorsulfonic acid (10.1 g), followed by heating and refluxing for additional 12 hours. The mixed reaction liquid was poured into a mixed liquid of EtOAc and water, and the organic layer was collected by separation. The organic layer was sequentially washed with water and saturated brine, and dried over anhydrous sodium sulfate. After the desiccant was removed, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel flash column chromatography (hexane-EtOAc) to obtain a mixture (7.46 g) of methyl 1-(tetrahydro-2H-pyran-2-yl)-1H-benzimidazole-5-carboxylate and methyl 1-(tetrahydro-2H-pyran-2-y1)-1H-benzimidazole-6-carboxylate.

The synthetic route of 26663-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; EP2325175; (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 26663-77-4 as follows. Application In Synthesis of Methyl benzimidazole-5-carboxylate

To a solution of methyl 1H-benzo[d]imidazole-5-carboxylate (0.90 g, 5.1 mmol) in DMF(20 ml) was added NaH (0.25 g, 6.2 mmol), and the reaction mixture was stirred at room temperature for 30 mm. Then (2-(chloromethoxy)ethyl)trimethylsilane (0.94 g, 5.6 mmol) wasadded and the reaction mixture was stirred at room temperature for 2 hours. When LCMS showed that the reaction completed, the reaction mixture was diluted with EtOAc (100 mL), washed with H20 (100 mL x 2) and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford crude product as an oil, which was purified by column chromatography on silica gel (eluted with petroleum ether/EtOAc = 1:1) to afford mixture ofmethyl 1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazole-5-carboxylate and methyl 1- ((2-(trimethylsilyl)ethoxy) methyl)- 1 H-benzo [d] imidazole-6-carboxylate as an oil. LC/MS (m/z): 307 (M+H).To a solution of LiA1H4 (0.30 g, 7.8 mmol) in THF (20 ml) was added solution of Step A product (1.2 g, 3.9 mmol) in THF (30 mL) at 0C, the reaction mixture was allowed to warm to room temperature and stirred for 3 hours. When TLC showed that the reaction completed, the reaction mixture was quenched with sat. aq. NH4C1 (50 mL) and the mixture was filteredthrough a pad of celite. The filtrate was extracted with EtOAc (100 mL), washed with H20 (100 mL) and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford mixture of (1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo [d] imidazol-5-yl) methanol and (1- ((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-6-yl)methanol as an oil, which was used in next step without further purification. ?H NMR (CDC13, 400 MHz) oe 8.03 (s, 1H), 8.02(s, 1H), 7.86-7.79 (m, 2H), 7.64 (s, 1H), 7.61-7.55 (m, 1H), 7.43 (d, J= 7.3 Hz, 1H), 7.36 (d, J=8.4 Hz, 1H), 5.59 (s, 4H), 4.90 (s, 2H), 4.87 (s, 2H), 3.59-3.53 (m, 4H), 0.99-0.91 (m, 4H), 0.00 (s, 9H).To a solution of Step B product (0.3 g, 1.1 mmol) in DCM(10 ml) was added SOC12 (0.8 ml, 10.8 mmol) dropwise at 0C, then the reaction mixture was stirred at room temperature for 3 hours. When TLC showed that the reaction completed, the reaction mixture was diluted with DCM (50 mL), washed with sat. aq. NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to afford a mixture of 5-(chloromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d] imidazole and 6-(chloromethyl)- 1 -((2- (trimethylsilyl) ethoxy)methyl)-1H-benzo[d]imidazole as an oil, which was used in next step without further purification. LC/MS (m/z): 297 (M+H).To a solution of Intermediate 2 (0.20 g, 0.65 mmol), Step C product (0.29 g, 0.97 mmol) in acetone (4 ml) and DMF (2 ml) was added K2C03(0.27 g, 1.9 mmol). The reaction mixture was then heated to 60 C and stirred for 6 hours. When LCMS showed that the reaction completed, the reaction mixture was diluted with EtOAc (1 OOmL), washed with H20 (100 mL)and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford crude product as an oil, which was purified by column chromatography on silica gel (eluted with Petroleum ether/EtOAc = 1:1) to afford a mixture of tert-butyl 2-(4-hydroxy-2-oxo-1-((1-((2- (trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-5 -yl)methyl)- 1,2,5 ,7-tetrahydrofuro [3,4- b]pyridine -3 -carboxamido)acetate and tert-butyl 2-(4-hydroxy-2-oxo- 1 -((1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-6-yl) methyl)- 1,2,5,7- tetrahydrofuro [3,4- b]pyridine-3-carboxamido)acetate as a solid. LC/MS (m/z): 571 (M+H).

According to the analysis of related databases, 26663-77-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; CAI, Jiaqiang; CRESPO, Alejandro; DU, Xiaoxing; DUBOIS, Byron Gabriel; LIU, Ping; LIU, Rongqiang; QUAN, Weiguo; SINZ, Christopher; WANG, Liping; (61 pag.)WO2016/49100; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-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. Safety of Methyl benzimidazole-5-carboxylate

The benzimidazole -5 – methyl formate (2.66 g, 15 . 12 mmol) is dissolved in 35 ml ethanol, adding hydrazine hydrate (8.6 ml, 120.9 mmol), 80 C reflux reaction for 36 hours, filtering, to obtain white solid, then the beating of ethyl acetate three times (3 × 15 ml), to obtain 1.8 g of white solid, yield 67.7%

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

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Wang Xiaojian; Sun Chenbin; Ge Jun; Xi Meiyang; Xiao Qiong; Yin Dali; (51 pag.)CN107151220; (2017); A;,
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. 26663-77-4, name is Methyl benzimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Preparation of ( 1 -methyl- l H-benzimidazol- – l methanolThe title compound was synthesized by esterification of l//-benzimidazole-5-carboxylic acid using methanol in presence of cone, sulphuric acid followed by N-methylation using methyl iodide in presence of potassium carbonate and subsequent reduction of the ester group by lithium aluminium hydride; NMR (300 MHz, DMSO- 6) delta 3.84 (s, 3H), 4.59 (s, 2H), 5.23 (br s, l H), 7.26 (d, J = 8.4 Hz, 1H), 7.52-7.58 (m, 2H), 8.23-8.31 (m, 1 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; GLENMARK PHARMACEUTICALS S.A.; LINGAM, Prasada, Rao, V., S.; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; BAJPAI, Malini; GULLAPALLI, Srinivas; DAHALE, Dnyaneshwar, Harishchandra; MINDHE, Ajit, Shankar; RATHI, Vijay, Eknath; WO2011/138657; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 26663-77-4, These common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-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.

Preparation of ( 1 -methyl- l H-benzimidazol- – l methanolThe title compound was synthesized by esterification of l//-benzimidazole-5-carboxylic acid using methanol in presence of cone, sulphuric acid followed by N-methylation using methyl iodide in presence of potassium carbonate and subsequent reduction of the ester group by lithium aluminium hydride; NMR (300 MHz, DMSO- 6) delta 3.84 (s, 3H), 4.59 (s, 2H), 5.23 (br s, l H), 7.26 (d, J = 8.4 Hz, 1H), 7.52-7.58 (m, 2H), 8.23-8.31 (m, 1 H).

The synthetic route of 26663-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; LINGAM, Prasada, Rao, V., S.; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; BAJPAI, Malini; GULLAPALLI, Srinivas; DAHALE, Dnyaneshwar, Harishchandra; MINDHE, Ajit, Shankar; RATHI, Vijay, Eknath; WO2011/138657; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem