Methanol → HCID 11639452, compound

Reaction equation

[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:35])=[C:11]([N:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([O:23][CH2:24][CH2:25][NH:26]C(=O)OC(C)(C)C)=[CH:18][CH:19]=4)[C:14]3=[O:34])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.CO>Cl.O1CCOCC1>[NH2:26][CH2:25][CH2:24][O:23][C:17]1[CH:16]=[C:15]2[C:20]([CH:21]=[CH:22][N:13]([C:11]3[CH:12]=[C:7]([CH:8]=[CH:9][C:10]=3[CH3:35])[C:5]([NH:4][CH:1]3[CH2:3][CH2:2]3)=[O:6])[C:14]2=[O:34])=[CH:19][CH:18]=1

Participants

Procedure

tert-Butyl {2-[(2-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1-oxo-1,2-dihydroisoquinolin-7-yl)oxy]ethyl}carbamate (145 mg) was dissolved in 4N HCl in dioxane (1.2 ml) and methanol (0.9 ml) stirred at room temperature for 18 hours. The orange solution was concentrated and purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK) using initially methanol and then a 99:1 mixture of methanol and aqueous ammonia solution to give 3-[7-(2-aminoethoxy)-1-oxoisoquinolin-2(1H)-yl]-N-cyclopropyl-4-methylbenzamide as a white solid (102 mg); NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 2.10 (s, 3H), 2.22 (s, 2H), 2.86 (m, 1H), 2.94 (t, 2H), 4.05 (m, 2H), 6.73 (d, 1H), 7.22 (d, 1H), 7.43 (m, 1H), 7.50 (d, 1H), 7.66 (d, 1H), 7.72 (d, 1H), 7.76 (d, 1H), 7.87 (m, 1H), 8.46 (d, 1H); Mass Spectrum: M+H+ 378.