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CAS No. : | 127406-55-7 | MDL No. : | MFCD01631910 |
Formula : | C12H9NO | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | NXZUVHZZIZHEOP-UHFFFAOYSA-N |
M.W : | 183.21 | Pubchem ID : | 3693046 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a 250 mL round-bottomed flask was added 4-(pyridin-3-yl)benzaldehyde (4 g, 21.8 mmol), <strong>[6633-61-0]methyl 2-aminothiazole-5-carboxylate</strong> (3.45 g, 21.83 mmol) and acetic acid (0.375 ml, 6.55 mmol) in toluene (109 ml). The reaction mixture was heated at reflux under Dean-Stark conditions for 3 hours, cooled to room temperature, and the volatiles were removed by rotary evaporation. Methanol was added, the solution was cooled to 0 C, and sodium borohydride (1.322 g, 34.9 mmol) was carefully added. The reaction was stirred at 0 C for 15 minutes and allowed to warm to room temperature while stirring for an additional 2 hour. The solids were filtered off, washed with water and dried under high vaccuum to give the title compound which was used in the next step without further purification. | ||
Example 2A methyl 2-(4-(pyridin-3-yl)benzylamino)thiazole-5-carboxylate To a 250 mL round-bottomed flask was added 4-(pyridin-3-yl)benzaldehyde (4 g, 21.8 mmol), <strong>[6633-61-0]methyl 2-aminothiazole-5-carboxylate</strong> (3.45 g, 21.83 mmol) and acetic acid (0.375 ml, 6.55 mmol) in toluene (109 ml). The reaction mixture was heated at reflux under Dean-Stark conditions for 3 hours, cooled to room temperature, and the volatiles were removed by rotary evaporation. Methanol was added, the solution was cooled to 0 C., and sodium borohydride (1.322 g, 34.9 mmol) was carefully added. The reaction was stirred at 0 C. for 15 minutes and allowed to warm to room temperature while stirring for an additional 2 hour. The solids were filtered off, washed with water and dried under high vacuum to give the title compound which was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | General procedure: To a glass vessel capable of being sealed with Teflon cap (for microwave vials) were added 1 and benzaldehyde derivative (3 equiv.). The vessel was capped and then, evacuated and backfilled with N2 (process repeated 3X). Anhydrous DMF (3.5mL/mmol) was introduced and the solution was vigorously stirred for 20min at-20C. TDAE was added slowly and the mixture was stirred for 1h. Then, the reaction was stirred at room temperature overnight. After LC-MS analysis clearly showed that the chloride had been totally consumed, the reaction was hydrolysed with distilled water. The mixture was then extracted with dichloromethane. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered off and concentrated under reduced pressure to afford the corresponding crude product 3. |
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