23687-26-5, 6-Aminoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
To (S)-3-[(tert-butoxycarbonyl)amino)]-2-(4-{[(2,4-dimethylbenzoyl) oxy]methyl}phenyl)propanoic acid (8) (2.3 g, 5.5 mmol) in DMF (33 mL) cooled to 0 ¡ãC was added 6-aminoisoquinoline (1.0 g, 7.1 mmol) and 2,4,6-trimethylpyridine (947 muL, 7.1 mmol). After 10 min at 0 ¡ãC, a solution of 2,2,2-trichloro-1,1-dimethylethyl chloroformate (1.7 g, 7.1 mmol) in DMF (8.6 mL) was added and the reaction stirred at 0 ¡ãC for 2 h. The mixture was poured into NaHCO3 (sat.)/EtOAc and extracted with EtOAc. The organic layers were then washed with NaCl (sat.), dried (Na2SO4) filtered and evaporated. Column chromatography (70percent EtOAc/hexanes) gave pure (S)-4-{3-[(tert-butoxycarbonyl) amino]-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl}benzyl 2,4-dimethylbenzoate (9) (1.93 g, 63percent, 98percent ee) as a off-white solid. Recrystallization from EtOAc/hexanes gave 9 (1.43 g, 47percent, 99.7percent ee, S,SWhelk-01) as a off-white crystalline solid. Mp 155-156 ¡ãC. IR (ATR): 1713, 1644, 1527 cm-1. 1H NMR (500 MHz, DMSO-d6): delta = 9.14 (s, 1H), 8.39 (d, J = 5.7 Hz, 1H), 8.38 (s, 1H), 8.02 (d, J = 8.7 Hz, 1H), 7.75 (d, J = 7.9 Hz, 1H), 7.69- 7.66 (m, 2 H), 7.43 (s, 4 H), 7.11 (s, 1H), 7.07 (d, J = 8.4 Hz, 1H), 7.02 (br t, J = 5.4 Hz, 1H), 5.25 (s, 2 H), 4.13-4.10 (m, 1H), 3.58-3.53 (m, 1H), 3.34-3.30 (m, 1H), 2.49 (s, 3 H), 2.29 (s, 3 H), 1.32 (s, 9 H). 13C NMR (125 MHz, DMSO-d6): delta = 171.0, 166.4, 155.8, 151.5, 143.2, 142.4, 140.4, 139.5, 137.8, 136.1, 135.2, 132.3, 130.4, 128.5, 128.1, 128.0, 126.6, 126.1, 125.0, 121.0, 120.0, 113.1, 77.8, 65.6, 51.7, 42.9, 28.2, 21.2, 20.8. LC-MS (ES+): m/z = 554 [M + 1]+, 576 [M + 23]+. Anal Calcd for C33H35N3O5: C, 71.59; H, 6.37; N, 7.59. Found: C, 71.54; H, 6.51; N, 7.58.
23687-26-5, The synthetic route of 23687-26-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Delong, Mitchell A.; Sturdivant, Jill M.; Synthesis; vol. 51; 4; (2019); p. 953 – 959;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem