Application of 3314-30-5, 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.
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°C, 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-fluoropyridin-2-yl)methyl]-1 ,3- thiazole-4-carboxamide dihydrochloride (192) (143 mg, 0.37 mmol), 1 H-1 ,3-benzodiazole-2-carbaldehyde (70.1 mg, 0.48 mmol), MgS04 (200 mg) in MeOH (10 ml) at room temperature for 3 d, followed by addition of NaBH4 (28 mg, 0.74 mmol) gave the title compound (94 mg, 56percent) as a white solid after purification by prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.19 (s, 1 H), 8.71 (t, J = 5.6 Hz, 1 H), 8.37 (dt, J = 4.6, 1.3 Hz, 1 H), 7.70 (ddd, J = 10.0, 8.4, 1.1 Hz, 1 H), 7.54 (d, J = 7.2 Hz, 1 H), 7.45 (d, J = 7.0 Hz, 1 H), 7.40 (dt, J = 8.6, 4.4 Hz, 1 H), 7.14 (t, J = 7.5 Hz, 2H), 4.66 – 4.58 (m, 2H), 3.97 (s, 2H), 3.12 (t, J = 6.3 Hz, 2H), 2.94 (t, J = 6.3 Hz, 2H) HPLCMS (Method A): [m/z]: 445.1 [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; 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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