23687-25-4, Isoquinolin-4-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
23687-25-4, General procedure: To a solution of 3 (100 mg, 0.18 mmol) in dry DCM (10 mL), oxalyl chloride (70 mg, 0.55 mmol), triethylamine (3 mg, 0.03 mmol) and DMF (2 mg, 0.03 mmol) were added, and the mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure, the residue was dissolved in dry THF (1 * 10 mL), the solvent was removed, and the residue was immediately dissolved in dry DCM (10 mL). The solution was cooled to 0 C and triethylamine (24 mg, 0.24 mmol), DMAP (2 mg, 0.02 mmol) as well as 3-aminopyridine (52 mg, 0.55 mmol) were added. After 2 days of stirring, Et2O (100 mL) was added, the organic was washed with diluted HCl (0.1 m, 1 * 100 mL), water (2 * 100 mL) and brine (1 * 50 mL), dried (MgSO4), filtrated and evaporated to dryness. Column chromatography (silica gel, hexane/ethyl acetate, 7:3) afforded 5 (85 mg, 75%) as a white solid; 4.2.242alpha, 3beta, 24-Triacetyloxy-ursan-12-en-28-oic acid 4-isoquinolinyl amide (28) As described for 5, compound 28 (53 mg, 44%) was obtained from 25 and 4-aminoisoquinoline as a white solid; m. p. 173-177 C; RF = 0.40 (silica gel, chloroform/ethyl acetate, 1:1); [alpha]D = -0.85 (c = 0.33, CHCl3); UV-vis (CHCl3): lambdamax (log epsilon) = 289 nm (3.68), 301 nm (3.67), 324 nm (3.72); IR (KBr): nu = 3396 m, 2948 m, 2926 m, 2870 m, 1746vs, 1684 m, 1626w, 1586w, 1522 m, 1488 m, 1456 m, 1370s, 1252vs, 1044 s cm-1; 1H NMR (500 MHz, CDCl3): delta = 9.08 (s, 1 H, H-38), 9.03 (s, 1 H, H-39), 8.00 (d, J = 8.2 Hz, 1 H, H-41), 7.91 (m, 1 H, NH), 7.77-7.72 (m, 2 H, H-44 + H-42), 7.63 (ddd, J = 8.0, 5.9, 2.0 Hz, 1 H, H-43), 5.56 (dd, J = 3.4, 3.4 Hz, 1 H, H-12), 5.14 (ddd, J = 10.5, 10.5, 4.5 Hz, 1 H, H-2), 5.07 (d, J = 10.3 Hz, 1 H, H-3), 3.82 (d, J = 11.8 Hz, 1 H, H-24a), 3.57 (d, J = 11.8 Hz, 1 H, H-24b), 2.22 (d, J = 10.1 Hz, 1 H, H-18), 2.15 (ddd, J = 13.6, 13.6, 4.2 Hz, 1 H, H-16a), 2.10-1.91 (m, 5 H, H-1a + H-11a + H-11b + H-22a + H-16b), 2.08 (s, 3 H, H-36), 2.01 (s, 3 H, H-34), 1.98 (s, 3 H, H-32), 1.86 (ddd, J = 14.4, 14.4, 4.4 Hz, 1 H, H-15a), 1.77 (ddd, J = 13.6, 13.6, 4.3 Hz, 1 H, H-22b), 1.69 (dd, J = 11.0, 6.6 Hz, 1 H, H-9), 1.62 (ddd, J = 13.3, 6.6, 3.2 Hz, 1 H, H-21a), 1.59-1.52 (m, 1 H, H-19), 1.50-1.28 (m, 6 H, H-7a + H-7b + H-21b + H-6a + H-6b + H-5), 1.20-1.04 (m, 3 H, H-15b + H-1b + H-20), 1.17 (s, 3 H, H-27), 1.02 (d, J = 6.3 Hz, 3 H, H-30), 1.00 (s, 3 H, H-25), 0.97 (d, J = 6.5 Hz, 3 H, H-29), 0.85 (s, 3 H, H-23), 0.73 (s, 3 H, H-26) ppm; 13C NMR (125 MHz, CDCl3): delta = 176.8 (C-28), 170.9 (C-35), 170.6 (C-31), 170.5 (C-33), 149.5 (C-39), 140.2 (C-13), 137.6 (C-38), 130.5 (C-42), 130.0 (C-37), 128.9 (C-40), 128.5 (C-41), 128.3 (C-45), 127.4 (C-43), 126.0 (C-12), 120.1 (C-44), 74.9 (C-3), 70.0 (C-2), 65.4 (C-24), 54.7 (C-18), 49.5 (C-17), 47.7 (C-5), 47.7 (C-9), 43.9 (C-1), 42.8 (C-14), 42.1 (C-4), 40.1 (C-19), 39.8 (C-8), 39.3 (C-20), 37.9 (C-10), 37.8 (C-22), 32.5 (C-7), 31.0 (C-21), 28.0 (C-15), 25.2 (C-16), 23.6 (C-11), 23.5 (C-27), 21.3 (C-30), 21.2 (C-32), 21.0 (C-36), 20.9 (C-34), 17.9 (C-6), 17.4 (C-26), 17.4 (C-29), 17.2 (C-25), 14.0 (C-23) ppm; MS (ESI): m/z (%) = 741.5 ([M+H]+, 100), 763.3 ([M+Na]+, 4), 1482.3 ([2 M + H]+, 92); analysis calculated for C45H60N2O7 (740.97): C 72.94, H 8.16, N 3.78; found: C 72.75, H 8.33, N 3.52.
The synthetic route of 23687-25-4 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Sommerwerk, Sven; Heller, Lucie; Kuhfs, Julia; Csuk, Rene; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 452 – 464;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem