Synthetic Route of 27489-62-9 ,Some common heterocyclic compound, 27489-62-9, molecular formula is C6H13NO, 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.
4.2.31 8-(trans-4-Hydroxycyclohexylamino)-1-(3-morpholinopropyl)oxazolo[4,5-g]quinazolin-2(1H)-one (6e) Trans-4-aminocyclohexanol (148 mg, 1.28 mmol) and TEA (150 mg, 2.14 mmol) was added to a solution of compound 13 (300 mg, 1.07 mmol) in isopropanol (12 ml) and stirred at 60 C for 24 h. The mixture was cooled to room temperature and concentrated in vacuo, the residue was 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 (90/1,v/v) gave 361 mg (yield, 79%) of the title compound as pale yellow solid: Mp: 312-315 C; HRMS, ESI+, m/z: Calcd for C22H30N5O4 (M + H)+, 428.2292; found, 428.2295; 1H NMR (500 MHz, DMSO-d6) delta:8.70 (1H, s), 7.80 (1H, s), 7.74 (1H, s), 4.14 (1H, s), 4.00 (2H, t, J = 6.4 Hz), 3.52 (4H, t, J = 4.2 Hz), 2.33 (2H, t, J = 6.3 Hz), 2.26 (4H, m), 2.00 (2H, p, J = 6.4 Hz); 13C NMR (75 MHz, DMSO-d6) delta:165.61, 159.43, 153.45, 153.26, 152.57, 152.00, 148.36, 148.27, 147.64, 147.03, 134.26, 132.23, 120.73, 112.49, 106.61, 106.06, 106.38, 101.58, 100.19, 66.00, 65.86, 55.01, 54.77, 54.15, 53.16, 53.12, 40.59, 40.33, 22.19, 22.91.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 27489-62-9, trans-4-Aminocyclohexanol, other downstream synthetic routes, hurry up and to see.
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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