Hydrochloric Acid → N1-(4-(4-amino-1H-pyrrolo[3,2-c]pyridin-1-yl)phenyl)-N3-(4-fluorophenyl)malonarnide
반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:37])[CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[C:28]4[CH:27]=[CH:26][N:25]=[C:24]([NH:29]C(=O)OC(C)(C)C)[C:23]=4[CH:22]=[CH:21]3)=[CH:16][CH:15]=2)=[O:12])=[CH:4][CH:3]=1.Cl>O1CCOCC1>[NH2:29][C:24]1[C:23]2[CH:22]=[CH:21][N:20]([C:17]3[CH:16]=[CH:15][C:14]([NH:13][C:11](=[O:12])[CH2:10][C:9]([NH:8][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[O:37])=[CH:19][CH:18]=3)[C:28]=2[CH:27]=[CH:26][N:25]=1참가 물질
4
실험 절차
tert-Butyl 1-(4-(3-(4-fluorophenylamino)-3-oxopropanamido)phenyl)-1H-pyrrolo[3,2-c]pyridin-4-ylcarbamate (37 mg, 0.074 mmol) was treated with 4 N HCl in dioxane (2 mL) and stirred at RT for 2 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between saturated NaHCO3 (2 mL) and EtOAc (2 mL). The EtOAc phase was separated, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, 10-15% MeOH-CHCl3 gradient elution) to afford the title compound (7.0 mg, 23%) as a white solid. 1H NMR (DMSO-d6) δ 10.58 (s, 1H), 10.38 (s, 1H), 8.01 (br s, 2H), 7.84 (d, 2H, J=9.0 Hz), 7.69-7.62 (m, 3H), 7.60 (d, 1H, J=7.4 Hz), 7.52 (d, 2H, J=9.0 Hz), 7.20-7.13 (m, 3H), 6.91 (d, 1H, J=8.2 Hz), 3.52 (s, 2H); LCMS (ESI+) m/z 404 (M+H)+; HPLC tR=2.98 min.