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

HRID 1162304Notes

Reaction equation

HRID 1162304 reaction equation
[CH3:1][C:2]1[N:6]2[C:7](=[O:33])[N:8]([CH:10]3[CH2:15][CH2:14][N:13]([C:16](=[O:32])[CH:17]([NH:24]C(=O)OC(C)(C)C)[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:12][CH2:11]3)[CH2:9][C:5]2=[CH:4][N:3]=1.C(OCC)(=O)C>Cl>[NH2:24][CH:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:16]([N:13]1[CH2:14][CH2:15][CH:10]([N:8]2[CH2:9][C:5]3=[CH:4][N:3]=[C:2]([CH3:1])[N:6]3[C:7]2=[O:33])[CH2:11][CH2:12]1)=[O:32]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 23138346tert-butyl 2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethylcarbamate

Product 1

HCID 231380962-(1-(2-amino-2-phenylacetyl)-4-piperidinyl)-5-methyl-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-oneYield 31%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-Butyl 2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethylcarbamate (0.43 g) obtained in Example 50a) was dissolved in concentrated hydrochloric acid (1.5 ml), and mixed at room temperature for 5 minutes. Ethyl acetate was added thereto, and the reaction mixture was washed with an aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as colorless powder (0.10 g, 31%).

Workup

  1. additionmixed at room temperature for 5 minutes
  2. washthe reaction mixture was washed with an aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a95b1b19816c4872abd5fbee45f0afaa
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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