Electric Literature of 121588-79-2, A common heterocyclic compound, 121588-79-2, name is trans-4-Methoxycyclohexanamine, molecular formula is C7H15NO, 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.
To a mixture of 5-chloro-6-ethyl-3-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino}pyrazine-2-carboxamide (11,100 mg, 0.205 mmol) and NMP (1.5 mL) was added (1r,4r)-4-methoxycyclohexan-1-amine (106 mg, 0.820 mmol), and the mixture was irradiated with microwaves at 200 C for 30 min. After the mixture was cooled, saturated aqueous NaHCO3 solution was added, and the resulting slurry was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo.The residue was purified by silica gel column chromatography (CHCl3/MeOH/28% aqueous NH3=100:0:0 to 200:10:1). The resulting product was solidified from EtOAc, filtered and dried to give 12c (62 mg,52%) as a yellow solid. 1H NMR (DMSO-d6): delta 1.10-1.28 (2H, m), 1.18(3H, t, J=7.4 Hz), 1.33-1.63 (4H, m), 1.73-1.86 (2H, m), 1.89-2.00(2H, m), 2.00-2.11 (2H, m), 2.14 (3H, s), 2.18-2.64 (11H, m), 2.56(2H, q, J=7.3 Hz), 3.05-3.19 (1H, m), 3.22-3.39 (2H, m), 3.26 (3H, s),3.75-3.95 (1H, m), 3.80 (3H, s), 6.66 (1H, d, J=7.6 Hz), 6.78 (1H, d,J=8.4 Hz), 7.05 (1H, d, J=2.4 Hz), 7.18 (1H, d, J=2.8 Hz), 7.24(1H, dd, J=2.4, 8.8 Hz), 7.50 (1H, d, J=2.8 Hz), 11.01 (1H, s); MS(ESI) m/z [M+H]+ 581; HRMS (ESI) m/z Calcd for C31H49N8O3[M+H]+: 581.3922, Found: 581.3924.
The synthetic route of 121588-79-2 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Iikubo, Kazuhiko; Kurosawa, Kazuo; Matsuya, Takahiro; Kondoh, Yutaka; Kamikawa, Akio; Moritomo, Ayako; Iwai, Yoshinori; Tomiyama, Hiroshi; Shimada, Itsuro; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1683 – 1692;,
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