Synthetic Route of 41406-00-2, A common heterocyclic compound, 41406-00-2, name is 3-Isopropoxyaniline, molecular formula is C9H13NO, its 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.
General procedure: 3-Chloro-4-fluoroaniline (172 mg, 1.18 mmol) was added to a solution of compound 13 (373 mg, 1.07 mmol) in isopropanol (10 ml) and stirred at reflux for 8 h. The mixture was cooled to room temperature and filtered, then the solid was washed with chill isopropanol (5 ml), treated with aqueous NaHCO3 (10 ml) and extracted with EtOAc/MeOH (20:1, 30 ml). The organic layer was washed with brine, dried over MgSO4, and concentrated. Chromatography of the residue on silica gel with DCM-MeOH (50/1, v/v) gave 416 mg (yield, 85%) of the title compound as white solid: 4.2.19 8-(3-Isopropoxyphenylamino)-1-(3-morpholinopropyl)oxazolo[4,5-g]quinazolin-2(1H)-one (5s) White solid, 416 mg, yield, 84%; Mp: 259-262 C; HRMS, ESI+, m/z: Calcd for C25H30F2N5O4 (M + H)+, 464.2292; found, 464.2285; 1H NMR (500 MHz, DMSO-d6) delta: 9.53 (1H, bs), 8.54 (1H, s), 8.24 (1H, s), 7.65 (1H, s), 7.50 (1H, s), 7.36 (1H, d, J = 8.6 Hz), 7.29 (1H, t, J = 8.1 Hz), 6.71 (1H, d, J = 8.6 Hz), 4.62 (1H, m), 3.99 (2H, t, J = 6.4 Hz), 3.41 (4H, m), 2.38 (2H, t, J = 6.5 Hz), 2.23 (4H, m), 2.00 (2H, p, J = 6.5 Hz), 1.31(6H, s); 13C NMR (125 MHz, DMSO-d6) delta:157.55, 157.07, 153.60, 152.99, 147.09, 146.34, 140.28, 131.12, 129.12, 114.34, 111.71, 110.01, 106.44, 100.33, 69.20, 65.92, 55.45, 53.25, 40.00, 22.86, 21.83.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Lin, Jinsheng; Shen, Wei; Xue, Jingwei; Sun, Juan; Zhang, Xue; Zhang, Can; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 39 – 48,10;,
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