Hydrochloric Acid → HCID 23138277, compound

HRID 1162306Notes

Reaction equation

HRID 1162306 reaction equation
C(O[C:6](=[O:32])[NH:7][CH:8]([C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:21][C:20]3=[CH:22][N:23]=[C:24]([CH3:25])[N:19]3[C:18]2=[O:26])[CH2:13][CH2:12]1)=[O:10])(C)(C)C.[ClH:33].C(O[CH2:38][CH3:39])(=O)C>>[Cl:33][C:39]1[CH:38]=[CH:9][C:8]([NH:7][C:6]([NH:7][CH:8]([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)[C:9]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[CH2:21][C:20]4=[CH:22][N:23]=[C:24]([CH3:25])[N:19]4[C:18]3=[O:26])[CH2:13][CH2:12]2)=[O:10])=[O:32])=[CH:27][CH:31]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 91557209HCID 91557209, compound

Product 1

HCID 23138277HCID 23138277, compoundYield 42%

Procedure

To tert-butyl(2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-(2-thienyl)ethyl)carbamate (0.32 g) obtained in Example Sib) was added a 4 N solution of hydrogen chloride in ethyl acetate (2.6 ml), mixed at room temperature for 5 minutes, and then concentrated under reduced pressure. The residue was dissolved in acetonitrile (5 ml), triethylamine (0.14 ml) and 4-chlorophenyl isocyanate (0.08 g) were added thereto, and mixed at room temperature for 3 hours. The solvent was 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 magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with basic silica gel column (ethyl acetate to ethyl acetate/methanol=10/1). The product was crystallized from ethyl acetate-diethyl ether to obtain the title compound as colorless powder (0.11 g, 42%).

Workup

  1. additionmixed at room temperature for 5 minutes
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in acetonitrile (5 ml)
  4. additiontriethylamine (0.14 ml) and 4-chlorophenyl isocyanate (0.08 g) were added
  5. additionmixed at room temperature for 3 hours
  6. distillationThe solvent was distilled off under reduced pressure
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washThe ethyl acetate solution was washed with an aqueous sodium hydrogen carbonate solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe residue was purified with basic silica gel column (ethyl acetate to ethyl acetate/methanol=10/1)
  12. customThe product was crystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-11b6470b792446609b029d2cd697b0e9
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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