Triethylamine → 1,2-Dihydro-5-methyl-2-(1-piperazinyl)-3H-imidazo[1,5-c]imidazol-3-one

HRID 1162300Notes

Reaction equation

HRID 1162300 reaction equation
[C:1]([O:5]C(NC(C(CC)(O)CC)C(O)=O)=O)(C)(C)C.C1C=C[C:22]2[N:27](O)[N:26]=[N:25][C:23]=2[CH:24]=1.[CH3:29][CH2:30][N:31]=C=NCCCN(C)C.C([N:42]([CH2:45][CH3:46])[CH2:43][CH3:44])C>C(#N)C>[CH3:29][C:30]1[N:25]2[C:1](=[O:5])[N:27]([N:26]3[CH2:44][CH2:43][NH:42][CH2:45][CH2:46]3)[CH2:22][C:23]2=[CH:24][N:31]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 23138330HCID 23138330, compound

Product 1

HCID 231384181,2-Dihydro-5-methyl-2-(1-piperazinyl)-3H-imidazo[1,5-c]imidazol-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-((tert-butoxycarbonyl)amino)-3-ethyl-3-hydroxypentanoic acid (0.80 g) obtained in Example 36b) and HOBt (0.65 g) in acetonitrile (30 ml) was added WSC (0.83 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 (0.63 g) obtained in Reference Example 2 and triethylamine (1.2 ml) 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 basic silica gel column (ethyl acetate) to obtain the title compound as colorless powder (0.11 g, 8%).

Workup

  1. additionthe reaction mixture was mixed at room temperature for 15 minutes

Sources & evidence

ORD record
ord-b9c161d8e5044e7fbc6d37465287313e
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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