Reference of 445-13-6,Some common heterocyclic compound, 445-13-6, name is 3-Chloro-4-(trifluoromethyl)aniline, molecular formula is C7H5ClF3N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To a solution of triphosgene (609 mg, 2.14 mmol) in toluene (5 mL) was added a solution of 3-chloro-4-(trifluoromethyl)aniline (100 mg, 0.51 mmol) and the mixture was refluxed at 80 C. for 0.5 h. After cooling to RT, the mixture was concentrated under vacuum and dissolved in THF (4 mL), then 3-(1-(aminomethyl)-4-oxo-4H-thieno[3,4-c]pyrrol-5(6H)-yl)piperidine-2,6-dione 2,2,2-trifluoroacetic acid (51.5 mg, 0.18 mmol) was added, followed by TEA (36 mg, 0.36 mmol). The solution was stirred at RT for 2 h then concentrated under vacuum and purified by prep-HPLC to give 1-(3-chloro-4-(trifluoromethyl)phenyl)-3-((5-(2,6-dioxopiperidin-3-yl)-4-oxo-5,6-dihydro-4H-thieno[3,4-c]pyrrol-1-yl)methyl)urea (18.6 mg, yield: 20.7%) as a white solid. MS (ESI) m/z 500.7, 502.6 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 10.98 (s, 1H), 9.35 (s, 1H), 7.87 (s, 1H), 7.69 (d, J=9.2 Hz, 1H), 7.43 (dd, J=7.2, 8.4 Hz, 1H), 7.11 (t, J=6.0 Hz, 1H), 5.01 (dd, J=8.0, 13.2 Hz, 1H), 4.40 (d, J=6.0 Hz, 2H), 4.28 (q, J=41.6 Hz, 2H), 2.93-2.84 (m, 1H), 2.73-2.60 (m, 1H), 2.37-2.26 (m, 1H), 2.07-1.97 (m, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-4-(trifluoromethyl)aniline, its application will become more common.
Reference:
Patent; BioTheryX, Inc.; Chan, Kyle W.H.; Erdman, Paul E.; Fung, Leah; Mercurio, Frank; Sullivan, Robert; Torres, Eduardo; (112 pag.)US2018/170948; (2018); A1;,
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