Related Products of 405173-97-9, 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. 405173-97-9, name is 2-(2-Chloroethyl)-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.
General procedure: 2-(2-Aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1 ,3-thiazole-4-carboxamide dihydrochloride (103) (2.0 g, 3.96 mmol) was added to a solution of 2-(2-chloroethyl)-1 H-1 ,3-benzodiazole hydrochbride (1.12 g, 5.15 mmol) and DIPEA (10.6 ml, 59.45 mmol) in DMF (60 ml). The reaction mixture was allowed to stir at 3GC for 6 d (reaction was monitored by LCMS). The mixture was concentrated in vacuo and the residue was neutralised using sat. NaHC03 (aq). The aqueous layer was extracted using 4: 1 CHCb / 1 PA (4 x 100 ml) and the combined organic layers were dried (MgS04), filtered and evaporated in vacuo. The crude residue was purified by flash column chromatography (kp-NH, eluting with a gradient of 60-100% EtOAc / heptane followed by 0-20% MeOH / EtOAc) follow by neutral reverse-phase column chromatography (gradient elution 0-60% MeCN / water) to give the title compound (0.173 g, 10%) as a yellow oil. 1 H-NMR (Methanol-d4, 500 MHz): d[ppm]= 8.31 (d, J = 4.6 Hz, 1 H), 8.02 (s, 1 H), 7.57 (t, J = 9.1 Hz, 1 H), 7.45 – 7.40 (m, 2H), 7.36 (dd, J = 8.6, 4.3 Hz, 1 H), 7.17 (dd, J = 6.0, 3.2 Hz, 2H), 4.68 (s, 2H), 3.26 (d, J = 6.8 Hz, 2H), 3.15 – 3.07 (m, 6H) HPLCMS (Method D): [m/z]: 425.1 [M+H]+In a similar fashion using general procedure 7, 1-(2-aminoethyl)-N-[(3-chloropyridin-2-yl)methyl]-1H- pyrazole-4-carboxamide dihydrochloride (261) (0.45 g, 1.28 mmol), 2-(2-chloroethyl)-1H-benzimidazole (0.28 g, 1.53 mmol) and DIPEA (3.3 ml, 19.14 mmol) in DMF (7 ml) at room temperature for 66 h, then heated to 40C for 90 h, gave the title compound (112 mg, 21%) as a colourless film after purification by flash column chromatography (kp-NH, eluting with a gradient of 0-10% MeOH / DCM) followed by basic prep-HPLC. 1H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.10 (s, 1H), 8.52-8.44 (m, 2H), 8.22 (s, 1H), 7.92 (dd, J = 8.1, 1.4 Hz, 1H), 7.90 (s, 1H), 7.55-7.38 (br m, 2H), 7.37 (dd, J = 8.1, 4.7 Hz, 1H), 7.13- 7.07 (m, 2H), 4.63 (d, J = 5.7 Hz, 2H), 4.20 (t, J = 6.2 Hz, 2H), 2.99- 2.93 (m, 4H), 2.93 – 2.89 (m, 2H) HPLCMS (Method C): [m/z]: 424.1 [M+H]
The chemical industry reduces the impact on the environment during synthesis 2-(2-Chloroethyl)-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.
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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