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;,
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