Triethylamine → 1,2-Dihydro-5-methyl-2-(1-piperazinyl)-3H-imidazo[1,5-c]imidazol-3-one
Reaction equation
ClC1C=CC(N[C:9](OC(C2C=CC=CC=2)C(O)=O)=[O:10])=CC=1.C1C=C[C:25]2[N:30](O)[N:29]=[N:28][C:26]=2[CH:27]=1.[CH3:32][CH2:33][N:34]=C=NCCCN(C)C.C([N:45]([CH2:48][CH3:49])[CH2:46][CH3:47])C>C(#N)C>[CH3:32][C:33]1[N:28]2[C:9](=[O:10])[N:30]([N:29]3[CH2:47][CH2:46][NH:45][CH2:48][CH2:49]3)[CH2:25][C:26]2=[CH:27][N:34]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ((((4-chlorophenyl)amino)carbonyl)oxy)(phenyl)acetic acid (0.31 g) obtained in Example 3b) and HOBt (0.23 g) in acetonitrile (10 ml) was added WSC (0.29 g), and the reaction mixture was mixed at room temperature for 15 minutes. Then, 5-methyl-2-(1-piperazinyl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one (0.22 g) obtained in Reference Example 2 and triethylamine (0.30 g) were added thereto. The reaction mixture was mixed at room temperature for 15 hours, the solvent was then distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with an aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified with silica gel column (ethyl acetate to ethyl acetate/methanol=5/1). The product was washed with diisopropyl ether to obtain the title compound as colorless powder (0.19 g, 37%).
Workup
- additionthe reaction mixture was mixed at room temperature for 15 minutes
Sources & evidence
- ORD record
- ord-12a47056020948f58f92cacd2b1776bb
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820673B2
Reaction notes
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