4-Methylmorpholine → 5-methyl-2-(4-piperidinyl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one

HRID 1162285Notes

Reaction equation

HRID 1162285 reaction equation
ClC1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:22])[NH:10][CH:11]([CH2:15]C2C=CC=CC=2)[C:12](O)=O)=[CH:4][CH:3]=1.C1C=C[C:26]2N(O)N=[N:29][C:27]=2C=1.CC[N:35]=C=NCCCN(C)C.CN1CCOCC1>CN(C=O)C>[CH3:26][C:27]1[N:10]2[C:9](=[O:22])[N:8]([CH:5]3[CH2:4][CH2:3][NH:35][CH2:7][CH2:6]3)[CH2:12][C:11]2=[CH:15][N:29]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 29747892-(N'-(4-chlorophenyl)ureido)-3-phenylpropanoic acid

Product 1

HCID 230840155-methyl-2-(4-piperidinyl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-oneYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(N′-(4-chlorophenyl)ureido)-3-phenylpropanoic acid (0.16 g) obtained in Example 1b) and HOBt (0.12 g) in DMF (10 ml) was added WSC (0.14 g), and the reaction mixture was mixed at room temperature for 15 minutes. Then, 5-methyl-2-(4-piperidinyl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one (0.11 g) obtained in Reference Example 1 and N-methylmorpholine (0.08 ml) were added thereto. The reaction mixture was mixed at room temperature for 15 hours, and then the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, 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=10/1). The product was washed with diethyl ether to obtain the title compound as colorless powder (0.13 g, 50%).

Workup

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

Sources & evidence

ORD record
ord-ecf8ae63a38846658d2af4150219f67d
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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