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

HRID 1162288
Notes
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Reaction equation

HRID 1162288 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 58840902HCID 58840902, compound

Product 1

HCID 231384181,2-Dihydro-5-methyl-2-(1-piperazinyl)-3H-imidazo[1,5-c]imidazol-3-oneYield 98.1%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

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

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

Sources & evidence

ORD record
ord-12a47056020948f58f92cacd2b1776bb
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07820673B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes