Hydrochloric Acid → HCID 58857996, compound

HRID 1162333Notes

Reaction equation

HRID 1162333 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[C@@H:3]([NH:22][C:23](=[O:29])OC(C)(C)C)[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[CH2:20][C:15]3=[N:16][C:17]([CH3:19])=[CH:18][N:14]3[C:13]2=[O:21])[CH2:8][CH2:7]1)=[O:5].[ClH:32].[CH2:33](O)[CH3:34]>>[Cl:32][C:34]1[CH:33]=[CH:10][C:9]([NH:12][C:23]([NH:22][C@@H:3]([C:4]([N:6]2[CH2:11][CH2:10][CH:9]([N:12]3[CH2:20][C:15]4=[N:16][C:17]([CH3:19])=[CH:18][N:14]4[C:13]3=[O:21])[CH2:8][CH2:7]2)=[O:5])[C:2]([CH3:1])([CH3:30])[CH3:31])=[O:29])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 131728396HCID 131728396, compound

Product 1

HCID 58857996HCID 58857996, compoundYield 53%

Procedure

To tert-butyl(1R)-2,2-dimethyl-1-((4-(2-methyl-5-oxo-5H-imidazo[1,5-a]imidazol-6(7H)-yl)-1-piperidinyl)carbonyl)propylcarbamate (0.17 g) obtained in Example 89c) was added a 40% solution of hydrogen chloride in ethanol (10 ml), and mixed for 1 hour. The reaction solution was concentrated under reduced pressure. The residue and triethylamine (0.16 ml) were dissolved in acetonitrile (15 ml) and a solution of 4-chlorophenyl isocyanate (72 mg) in acetonitrile (15 ml) was added dropwise thereto. The reaction mixture was mixed for 15 hours, then 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 recrystallized from diethyl ether to obtain the title compound as colorless powder (0.17 g, 53%).

Workup

  1. additionmixed for 1 hour
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionThe residue and triethylamine (0.16 ml) were dissolved in acetonitrile (15 ml)
  4. additiona solution of 4-chlorophenyl isocyanate (72 mg) in acetonitrile (15 ml) was added dropwise
  5. additionThe reaction mixture was mixed for 15 hours
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was purified with silica gel column (ethyl acetate to ethyl acetate/methanol=5/1)
  8. customThe product was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-8f52160a590a4ce284f216f9da67858f
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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