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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1162359Generated: October 26, 2026

Phenyl isocyanate → (2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethyl)-N'-phenylurea

https://huagongshe.com/reaction/1162359

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhenyl isocyanateHCID 7672—
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
Reactant2-(1-(2-amino-2-phenylacetyl)-4-piperidinyl)-5-methyl-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochlorideHCID 23138338—
SolventAcetonitrileHCID 6342—
Product(2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethyl)-N'-phenylureaHCID 2313809960.1%

Reaction Steps

2-(1-(2-Amino-2-phenylacetyl)-4-piperidinyl)-5-methyl-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochloride (0.21 g) obtained in Example 115a) and DBU (0.15 g) were dissolved in acetonitrile (10 ml). Phenyl isocyanate (66 mg) was added thereto, and mixed at room temperature for 2 hours. The solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate. The reaction mixture 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) and solidified with ethyl acetate and diethyl ether to obtain the title compound (0.14 g, 59%) as colorless powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07820673B2
Source datasetuspto-grants-2010_10
ORD IDord-aca0fecb0d7744108324ac6a1f97e603
Source noteuspto-grants-2010_10