1535-73-5, 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 1535-73-5 as follows.
To a solution of 4-[2-(propargylamino)-2-oxo-acetyl]-1,3,5-trimethyl-pyrrol- 2-carboxylic acid 6 (250 mg, 1.0 mmol), 3-(trifluoromethoxy)aniline (227 mg, 1.3 mmol) and DIPEA (330 muL, 2.0 mmol) in pyridine (10 mL) was added HATU (0.65 g, 1.8 mmol) at room temperature. The mixture was stirred at 65 ¡ãC for 18 h. The reaction mixture was then poured into a saturated solution of ammonium chloride and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (Hexanes:EtOAc = 6:4 v/v) to give compound 55 as a white powder (34percent, 135 mg, 0.3 mmol). 1H NMR (400 MHz, Acetone-d6) delta 9.57 (s, 1H), 8.18 (s, 1H), 8.02 (s, 1H), 7.81? 7.67 (m, 1H), 7.50 (t, J = 8.2 Hz, 1H), 7.16? 7.06 (m, 1H), 4.17 (dd, J = 5.8, 2.6 Hz, 2H), 3.71 (s, 3H), 2.75 (t, J = 2.5 Hz, 1H), 2.45 (s, 3H), 2.32 (s, 3H). MS (ESI): m/z [M+H]+ calcd for C20H19F3N3O4: 422.4, found: 422.4.
According to the analysis of related databases, 3-Trifluoromethoxyaniline, the application of this compound in the production field has become more and more popular.
Reference:
Patent; EMORY UNIVERSITY; SCHINAZI, Raymond F.; BOUCLE, Sebastien; AMBLARD, Franck; SARI, Ozkan; BASSIT, Leda; (169 pag.)WO2017/156255; (2017); A1;,
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