Hydrochloric Acid → HCID 56941127, compound

Reaction equation

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

Participants

Procedure

6N HCl (5 mL) was added drop wise to a solution of 1-acetyl-7-(4-methylpyridin-3-yl)-6,7-dihydro-1H-pyrazolo[4,3-g]isoquinolin-8(5H)-one (I-69h: 80 mg, 0.249 mmol) in methanol (5 ml) at 0° C. and the resulting reaction mass was stirred at room temperature for 36 hours. The reaction was monitored by TLC (100% ethyl acetate). The reaction mass was concentrated under reduced pressure, basified using saturated NaHCO3 solution and extracted using ethyl acetate. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (100% ethyl acetate), followed by preparative HPLC afforded 8 mg of the product (11.5% yield).