HCID 59841049, compound → HCID 178423961, compound
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:38])[N:5]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:6]([CH:12]([O:14][C:15]1[N:23]=[CH:22][N:21]=[C:20]3[C:16]=1[N:17]=[CH:18][N:19]3COCC[Si](C)(C)C)[CH3:13])=[N:7]2>CO.Cl>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:38])[N:5]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:6]([CH:12]([O:14][C:15]1[N:23]=[CH:22][N:21]=[C:20]3[C:16]=1[N:17]=[CH:18][NH:19]3)[CH3:13])=[N:7]2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
Compound 182 (0.053 g, 0.1 mmol) was dissolved in a mixture of methanol (2 mL) and 4M HCl (2 mL). The mixture was stirred and heated to 40° C. for 3 h. The reaction mixture was removed from the heat source and allowed to cool. The reaction mixture was then filtered through a plug of GFA (glass fiber) filter paper and the filtrate concentrated to only remove the methanol. The residue was adjusted to pH 10 by addition of 10% potassium carbonate solution. The resulting solid was collected by filtration and purified by RP-HPLC (C18 Luna column, 10×250 mm, 4.7 mL/min, 10-90% CH3CN in water in 18 min, with all solvents containing 0.05% formic acid) to give compound 176 as a fluffy white solid after lyophilization. 1H NMR (400 MHz, d6-DMSO) δ 13.40, br s, 1H, 8.40, s, 1H, 8.35, s, 1H; 7.66, t, J=7.8 Hz, 1H, 7.48-7:58, m, 4H; 7.31-7.36, m, 2H, 7.20-7.23, m, 1H, 5.65, q, J-6.6 Hz, 1H, 2.73, s, 3H, 1.65, d, J=6.6 Hz, 3H. ESI-MS m/z=399 (MH+). The reaction, described above and compound 176 are shown below.