Category: 5805-57-2

5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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. Recommanded Product: (1H-Benzo[d]imidazol-2-yl)methanamine

(R/5)-2-Hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)- l,2,4-oxadiazol-3-yl)phenyl)acetic acid (Int-V, 20 mg, 0.046 mmol), (1H- benzo[d]imidazol-2-yl)methanamine (10.24 mg, 0.070 mmol), HATU (22.92 mg, 0.060 mmol), and 4-methylmorpholine (18.76 mg, 0.185 mmol) were added to DMF (1 mL). This was stirred for 1 h before it was purified via preparative LCMS with the following conditions: Column: Waters XBridge C18, 19 x 250 mm, 5-muiotaeta particles; Guard Column: Waters XBridge CI 8, 19 x 10 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 methanohwater with 10-mM ammonium acetate; Mobile Phase B: 95:5 methanol: water with 10-mM ammonium acetate; Gradient: 45-100% B over 25 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give (R/5)-N- ((lH-benzo[d]imidazol-2-yl)methyl)-2-hydroxy-2-(4-(5-(3-phenyl-4- (trifluoromethyl)isoxazol-5-yl)-l,2,4-oxadiazol-3-yl)phenyl)acetamide (12.8 mg, 0.023 mmol, 49.3 % yield): LCMS = 561.1 [M+H]+; ‘H NMR (400 MHz, methanol- cU) 5 ppm 8.19 (2 H, d, J=8.58 Hz), 7.51-7.79 (10 H, m), 7.34 (2 H, dd, J=6.05, 3.19 Hz), 5.27 (1 H, s), 4.76-4.94 (2 H, m); HPLC peak RT = 2.6 min (Method E).

The synthetic route of 5805-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHERNEY, Robert J.; ZHANG, Yanlei; WO2011/133734; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5805-57-2, These common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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: Compound 7 (0.5mmol) and DIPEA (0.7mmol) were mixed in anhydrous DMF (4mL) at 0C. After 45min, HBTU (0.6mmol) followed by the amine partner (8a-s; 0.55mmol) were added and stirring was continued at room temperature for 10-13h. After completion, the reaction mixture was diluted with EtOAc and washed with cold water and followed by brain solution. Then, the organic layer was dried over Na2SO4 and concentrated under the vacuum to obtain the crude product. Then, the residue was purified on flash chromatography using EtOAc/hexane or MeOH/DCM as eluent to obtain the title compounds 9a-s.

The synthetic route of 5805-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Omar, Hany A.; Zaher, Dana M.; Srinivasulu, Vunnam; Hersi, Fatema; Tarazi, Hamadeh; Al-Tel, Taleb H.; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 804 – 814;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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. HPLC of Formula: C8H9N3

General procedure: Starting amino compound (0.238 mmol) was dissolved in THF (25 mL) and triethylamine (10 drops) was added to the stirred solution. Acyl halide (0.149 mmol) was added dropwise to the stirred solution, which was then heated under reflux for 3h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc and washed with aq. K2CO3 solution followed by brine. The organic layer was then dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 1-5 methanol/DCM v/v.

The synthetic route of (1H-Benzo[d]imidazol-2-yl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Elshihawy, Hosam; Helal, Mohamed A.; Said, Mohamed; Hammad, Mohamed A.; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 550 – 558;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5805-57-2, These common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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: 9-Chloroacridine or its derivatives (1.0 mmol) and phenol (10.0 mmol) were added into a 100 ml round-bottom flask and the mixture was stirred for 1 h at 60 C under argon atmosphere. Then benzimidazole derivatives (8a-8n, 8p-8q, 1.2 mmol) were added. The mixture was stirred under 120 C for 2 h. Then the mixture was poured into a mixture of ethyl acetate (50 mL) and N-methyl morpholine (1 ml) to get the crude product as yellow precipitation. The crude product was recrystallized from ethylacetate.

The synthetic route of 5805-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Chunmei; Li, Bin; Zhang, Bin; Sun, Qinsheng; Li, Lulu; Li, Xi; Chen, Changjun; Tan, Chunyan; Liu, Hongxia; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1800 – 1807;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 5805-57-2, 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. 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of C-(1H-benzoimidazol-2-yl)-methylamine (200 mg, 1.0 mmol) and triethylamine (139 muL, 1 mmol) in CH2Cl2 (5 mL) (Boc)2O (420 mg, 2 mmol) is added, and the reaction mixture is stirred at r.t. for 1 h. After solvent evaporation, the crude product is purified by flash chromatography (1:1 EtOAc-Et.petr., Rf=0.5), to give 2-(tert-butoxycarbonylamino-methyl)-benzoimidazole-1-carboxylic acid t-butyl ester as a yellow oil (246 mg, 0.71 mmol) in 71.% yield. 1H NMR (CDCl3, 200 MHz) epsilon 7.96-7.91 (m, 1H), 7.72-7.67 (m, 1H), 7.35-7.26 (m, 2H), 5.85 (br, 1H), 4.80 (d, 2H), 1.71 (s, 9H), 1.48 (s, 9H) ppm. This intermediate (175 mg, 0.5 mmol) is dissolved in anhydrous THF (10 mL) and PPh3 (330 mg, 0.5 mmol) and 4-pentynol (46 muL, 0.5 mmol) are added. Then, after cooling to 0 C., DIAD (100 muL, 0.5 mmol) is slowly added, and after 15 min at 0 C., the mixture is heated under microwave irradiation at 110 C. for 1 h. Following flash chromatography purification (5:1 EtOAc-petr. et.), compound 10 is obtained in 64% yield. 1H NMR (CDCl3, 200 MHz) delta 7.95-7.90 (m, 1H), 7.71-7.67 (m, 1H), 7.34-7.26 (m, 2H), 5.79 (d, 2H), 2.30-2.20 (m, 2H), 2.03 (s, 1H), 1.95-1.92 (m, 2H), 1.80 (t, 2H), 1.71 (s, 9H), 1.47 (s, 9H) ppm.

The chemical industry reduces the impact on the environment during synthesis (1H-Benzo[d]imidazol-2-yl)methanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITA’ DEGLI STUDI DI FIRENZE; Guarna, Antonio; Menchi, Gloria; Cini, Nicoletta; Trabocchi, Andrea; Pupi, Alberto; Bottoncetti, Anna; Raspanti, Silvia; Calorini, Lido; US2013/40964; (2013); 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. 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, A new synthetic method of this compound is introduced below., Recommanded Product: (1H-Benzo[d]imidazol-2-yl)methanamine

The residue was dissolved in DMF and EDC (0.5 mmol), HOBt (0.5 mmol), DIPEA (1.0 mmol), (lH-benzo[d]imidazol-2-yl)methanamine (0.5 mmol) were added. The solution was stirred at room temperature overnight and then removed under vacuum. The residue was dissolved in EtOAc (25 mL). The organic layer was washed with water, brine (25 mL), dried and concentrated under vacuum. The residue was chromatographed to give N-((1H- be^o[d]irmdazol-2-yl)methyl)-2-(5,7-dichlorobenzofuran-2-yl)acetamide (1756). LC/MS: (ESI) (M +H)+= 375.6.

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; UNIVERSITY OF WASHINGTON; BUCKNER, Frederick, S.; ALVAREZ, Ximena, Barros; FAN, Erkang; GILLESPIE, John, Robert; HOL, Wilhelmus, G.J.; HUANG, Wenlin; KOH, Cho, Yeow; RANADE, Ranae, M.; SHIBATA, Sayaka; VERLINDE, Christophe, L.M.; ZHANG, Zhongsheng; (249 pag.)WO2016/29146; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5805-57-2,Some common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, molecular formula is C8H9N3, 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: 9-Chloroacridine or its derivatives (1.0 mmol) and phenol (10.0 mmol) were added into a 100 ml round-bottom flask and the mixture was stirred for 1 h at 60 C under argon atmosphere. Then benzimidazole derivatives (8a-8n, 8p-8q, 1.2 mmol) were added. The mixture was stirred under 120 C for 2 h. Then the mixture was poured into a mixture of ethyl acetate (50 mL) and N-methyl morpholine (1 ml) to get the crude product as yellow precipitation. The crude product was recrystallized from ethylacetate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1H-Benzo[d]imidazol-2-yl)methanamine, its application will become more common.

Reference:
Article; Gao, Chunmei; Li, Bin; Zhang, Bin; Sun, Qinsheng; Li, Lulu; Li, Xi; Chen, Changjun; Tan, Chunyan; Liu, Hongxia; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1800 – 1807;,
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. 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (1H-Benzo[d]imidazol-2-yl)methanamine

General procedure: To the triazole carbamate ester of MMB (7) (0.167 mmol) indichloromethane (2 mL) was added the appropriate imidazole orbenzimidazole amine (0.167 mmol) at ambient temperature, andthe reaction mixture was stirred for 4-16 h. After completion ofthe reaction (monitored by TLC), water was added and the resultingmixture extracted with dichloromethane. The organic liquorswere separated, washed with water, followed by brine solution,dried over anhydrous Na2SO4, filtered, and the solvent removedto afford the crude reaction product. The crude product was purifiedby column chromatography (silica gel, 2-5% methanol indichloromethane) to afford the appropriate carbamate derivativeof MMB as a white solid (yield: 65-75%).

According to the analysis of related databases, 5805-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Albayati, Zaineb A.F.; Janganati, Venumadhav; Chen, Zheng; Ponder, Jessica; Breen, Philip J.; Jordan, Craig T.; Crooks, Peter A.; Bioorganic and Medicinal Chemistry; vol. 25; 3; (2017); p. 1235 – 1241;,
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 5805-57-2 as follows. Product Details of 5805-57-2

General procedure: 9-Chloroacridine or its derivatives (1.0 mmol) and phenol (10.0 mmol) were added into a 100 ml round-bottom flask and the mixture was stirred for 1 h at 60 C under argon atmosphere. Then benzimidazole derivatives (8a-8n, 8p-8q, 1.2 mmol) were added. The mixture was stirred under 120 C for 2 h. Then the mixture was poured into a mixture of ethyl acetate (50 mL) and N-methyl morpholine (1 ml) to get the crude product as yellow precipitation. The crude product was recrystallized from ethylacetate.

According to the analysis of related databases, 5805-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gao, Chunmei; Li, Bin; Zhang, Bin; Sun, Qinsheng; Li, Lulu; Li, Xi; Chen, Changjun; Tan, Chunyan; Liu, Hongxia; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1800 – 1807;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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 5805-57-2, Safety of (1H-Benzo[d]imidazol-2-yl)methanamine

To a stirred solution of (S)-methyl 2~amino-3~(2,4~ dichiorophenylipropanoate (103 mg, 0.415 mmol) in DCM (10 mL) was added DIPEA ( 1.5 equiv) and cooled to 0 C. A solution of triphosgene (0.33 equiv) in DCM (2 mL) was added dropwise to the reaction mixture and stirred at room temperature for 2 h. The solution was 106 back to 0 C and ( lH-benzo[d]imidazol-2-yl)niethanamine (1.5 equiv) in DCM (2 nil) was added. The reaction mixture was stirred at 0 C for 30niin. The solution washed with brine, dried over anhydrous sodium sulfate and evaporated under vacuum. The residue was purified by flash column chromatography to give (S)-methyi 2-(3-(( lH-benzo[dJimidazol-2- yl)methyl)ureido)-3-(2,4-dich{orophenyl)propanoate.

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]imidazol-2-yl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF WASHINGTON; BUCKNER, Frederick, S.; ALVAREZ, Ximena, Barros; FAN, Erkang; GILLESPIE, John, Robert; HOL, Wilhelmus, G.J.; HUANG, Wenlin; KOH, Cho, Yeow; RANADE, Ranae, M.; SHIBATA, Sayaka; VERLINDE, Christophe, L.M.; ZHANG, Zhongsheng; (249 pag.)WO2016/29146; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem