Hydrochloric Acid → 1-Methyl-1H-imidazole-2-carbohydrazide
Reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([NH:9][NH:10]C(OC(C)(C)C)=O)=[O:8].Cl>O1CCOCC1>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([NH:9][NH2:10])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of t-butyl 2-[(1-methyl-1H-imidazol-2-yl)carbonyl]hydrazinecarboxylate (I45) (143 mg, 0.595 mmol) in 1,4-dioxane (1.5 ml) stirred under argon at room temp was added a solution of hydrochloric acid (4 M) in dioxane (2.232 ml, 8.93 mmol). The reaction mixture was stirred at RT for 48 hr, then evaporated in vacuo and the residue added to an SCX column and eluted with dichloromethane (100 ml) followed by 5% MeOH/DCM (50 ml), 10% MeOH/DCM (30 ml), and 2M NH3/MeOH (50 ml) to afford the required product as a chartreuse solid in 73.1 mg, which was used without further purification in the next step.