Category: 3314-30-5

Electric Literature of 3314-30-5, A common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, molecular formula is C8H6N2O, 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: 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 to general procedure 3, -(2-aminoethyl)-N’-[(3-fluoropyridin-2- yl)methyl]propanediamide (418) (190 mg , 0.75 mmol), 1 H-1 ,3-benzodiazole-2-carbaldehyde (120 mg, 0.82 mmol) and MgS04 (100 mg) in DCM (10 ml) and MeOH (5 ml) at room temperature for 16 h, followed by addition of NaBH4 (57 mg , 1 .51 mmol) gave the title compound (87 mg, 28percent) as a pale yellow solid after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.14 (s, 1 H), 8.59 (t, J = 5.5 Hz, 1 H), 8.40 – 8.35 (m, 1 H), 8.06 (t, J = 5.5 Hz, 1 H), 7.69 (m, 1 H), 7.57 – 7.47 (m, 1 H), 7.47 – 7.36 (m, 2H), 7.16 – 7.08 (m, 2H), 4.48 (dd, J = 5.5, 1 .7 Hz, 2H), 3.91 (s, 2H), 3.20 (dt, J = 6.5, 6.5 Hz, 2H), 3.13 (s, 2H),2.63 (t, J = 6.5 Hz, 2H) HPLCMS (Method C): [m/z]: 385.2 [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; 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

3314-30-5, A common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, molecular formula is C8H6N2O, 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.

Typical procedure for the preparation of Benzimidazolyl-benzimidazole; A solution of benzimidazole-2-aldehyde 1 (0.5 mmol) and diamine 2 (0.5 mmol) in dimethylacetamide (4mL) was stirred at 100 0C for 12h. Solvent was evaporated and residue was purified by preparative HPLC to give benzimidazole derivative 3. 1H NMR (300 MHz, MeOH-doe : S 2.52 (s, 3H), 2.85 (brs, 4H)5 3.25 (brs, 4H)5 7.05-7.15 (m, 2 H), 7.25-7.35 (s overlapped with m, 2 H)5 7.60-7.75 (m, 4H); LCMS mlz 333 (M + H+), ELSD 99percent.

The synthetic route of 3314-30-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMBRIDGE RESEARCH LABORATORIES, INC.; WO2007/56155; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3314-30-5, Adding a certain compound to certain chemical reactions, such as: 3314-30-5, name is 1H-Benzo[d]imidazole-2-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 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 to general procedure 3, 2-(2-aminoethyl)-5-chloro-N-[(5-methylpyrimidin-2-yl)methyl]- 1 ,3-thiazole-4-carboxamide dihydrochloride (197) (223 mg, 0.52 mmol), 1 H-benzimidazole-2-carbaldehyde (99 mg, 0.68 mmol), DIPEA (0.363 ml, 2.09 mmol) and MgSQ (400 mg) in MeOH (6 ml) at room temperature for 24 h, followed by addition of NaBH4 (30 mg, 0.78 mmol) gave the title compound (120 mg, 52percent) as a white solid after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.21 (s, 1 H), 8.72 (t, J = 5.8 Hz, 1 H), 8.63 – 8.57 (m, 2H), 7.50 (s, 1 H), 7.14 (dd, J = 6.0, 2.7 Hz, 2H), 4.61 – 4.56 (m, 2H), 3.98 (s, 2H), 3.13 (t, J = 6.3 Hz, 2H), 2.95 (t, J = 6.3 Hz, 2H), 2.75 (s, 1 H), 2.26 (s, 3H) HPLCMS (Method C): [m/z]: 442 [M+H]+

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, 1H-Benzo[d]imidazole-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

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

Adding a certain compound to certain chemical reactions, such as: 3314-30-5, name is 1H-Benzo[d]imidazole-2-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 3314-30-5, 3314-30-5

General procedure: The following compounds were prepared following a reductive amination procedurelike the one described for the preparation of product 20 starting from the corresponding amine and aldehyde intermediates using sodium triacetoxyborohydride in DCM.Changes of solvent, reductant are mentioned in the Table below. In the case a base or acid was used this is also noted in the Table A below.

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, 1H-Benzo[d]imidazole-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose, Manuel; TRABANCO-SUAREZ, Andres, Avelino; ALCAZAR-VACA, Manuel, Jesus; MARTINEZ VITURRO, Carlos, Manuel; TRESADERN, Gary, John; ZHANG, Wei; CHEN, Gang; (212 pag.)WO2018/109202; (2018); A1;,
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

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 3314-30-5 as follows. 3314-30-5

To a mixture of X4-011-1 (2 g, 12.4 mmol) and 1H-benzo[d]imidazole-2- carbaldehyde (2.72 g, 18.6 mmol) in MeOH (60 ml) was added a solution of NaOH (992 mg, 24.8 mmol) in H20 (4 ml) at 0 ¡ãC and the mixture was stirred at room temperature for 3 h. The solution was adjusted pH to 8 with 35percent HC1 aq., dried over anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by column chromatography to give X4-011-2 (2.7 g, 75.2 percent yield) as a yellow solid. LCMS (Agilent LCMS 1200-6110, Column: Waters XBridge C18 (50 mm*4.6 mm*3.5 jim); Column Temperature: 40 ¡ãC; Flow Rate: 2.0 mL/min; Mobile Phase: from 95percent [0.05percent aq. TFA] and 5percent [CH3CN + 0.05percent TFA] to 0percent [0.05percent aq. TFA] and 100percent [CH3CN + 0.05 percent TFA] in 1.6 mm, then under this condition for 1.4 mm, finally changed to 95percent [0.05percent aq. TFA] and 5percent [CH3CN + 0.05percent TFA] in 0.05 mm and under this condition for 0.7 mi. Purity: 99percent; Rt = 1.32 mm; MS Calcd.: 289.1; MS Found: 290.1 [M+H].

According to the analysis of related databases, 3314-30-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; X4 PHARMACEUTICALS, INC.; BOURQUE, Elyse Marie Josee; SKERLJ, Renato; (279 pag.)WO2017/223229; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3314-30-5, 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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 19 Synthesis of 2-benzimidazolecarbaldehyde-(5-nitro-2-pyridyl)hydrazone (compound 19) A desired product was obtained in the same manner as in Example 1 by using 3.20 g (20.8 mmol) of 5-nitro-2-pyridylhydrazine and 2.90 g (19.8 mmol) of 2-benzimidazolecarbaldehyde. Yield: 4.80 g (17.0 mmol) [yield rate: 86percent] Melting point: 310¡ã to 311¡ã C.

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; Kabushiki Kaisha Toshiba; US5569763; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3314-30-5, Adding some certain compound to certain chemical reactions, such as: 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, 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 3314-30-5.

General procedure: The equimolar aldehyde 3a?3d (1 mmol) and substituted phenylhydrazine 5a?5s (1 mmol) weremixed in CH3OH (10 mL) and stirred at room temperature [18]. After about 2 h, the reaction wascompleted (monitored by TLC). The residual crude was purified via silica gel column chromatogramusing a gradient mixture of petroleum ether and ethyl acetate to obtain the pure target compounds6a?6ai (in 45?80percent yield).

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 3314-30-5.

Reference:
Article; Wang, Xing; Chen, Yong-Fei; Yan, Wei; Cao, Ling-Ling; Ye, Yong-Hao; Molecules; vol. 21; 11; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3314-30-5, 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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, A new synthetic method of this compound is introduced below.

A mixture of (S)-(+)-2-(diphenylphosphine oxide)-1,1′-binaphthyl-2′-amine 6 (200 mg, 0.426 mmol) and 2-formyl-1H-benzoimidazole (187 mg, 1.278 mmol) in the presence of 4 A MS (0.85 g) in dry toluene (8 mL) was stirred at 110 ¡ãC for 14 h in a pressure tube.

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:
Article; Eliseenko, Sviatoslav S.; Liu, Fei; Tetrahedron; vol. 75; 4; (2019); p. 518 – 526;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3314-30-5, 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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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 to general procedure 3, 2-(2-aminoethyl)-5-chloro-N-[(3-chloropyridin-2-yl)methyl]-1 ,3- thiazole-4-carboxamide dihydrochloride (193) (320 mg, 0.79 mmol), 1 H-1 ,3-benzodiazole-2-carbaldehyde (127.3 mg, 0.87 mmol), DIPEA (0.32 ml, 2.0 mmol) and MgSQ (300 mg) in MeOH (20 ml) at room temperature for 16 h, followed by addition of NaBh (60 mg, 1.59 mmol) gave the title compound (191 mg, 52percent) as a white solid after purification by prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.18 (s, 1 H), 8.72 (t, J = 5.6 Hz, 1 H), 8.49 (dd, J = 4.7, 1.3 Hz, 1 H), 7.95 (dd, J = 8.1 , 1 .3 Hz, 1 H), 7.54 (s, 1 H), 7.46 (s, 1 H), 7.38 (dd, J = 8.1 , 4.7 Hz, 1 H), 7.17- 7.09 (m, 2H), 4.65 (d, J = 5.5 Hz, 2H), 3.98 (d, J = 4.1 Hz, 2H), 3.13 (t, J = 6.3 Hz, 2H), 2.95 (q, J = 6.1 , 5.3 Hz, 2H, 2.74 (s, 1 H) HPLCMS (Method C): [m/z]: 461 [M+H]+

The synthetic route of 1H-Benzo[d]imidazole-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

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