Hydrochloric Acid → Ethyl 10-(ethylamino)-4-oxo-3-((phenylcarbonyl)oxy)-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate

HRID 1093085Notes

Reaction equation

HRID 1093085 reaction equation
[CH2:1]([N:8](CC)[C:9]12[CH2:17][CH2:16][CH:13]([CH2:14][CH2:15]1)[CH2:12][N:11]1[C:18](=[O:36])[C:19]([O:27][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:29])=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:21]=[C:10]21)[C:2]1C=CC=CC=1.Cl.[H][H]>CO.[Pd]>[CH2:1]([NH:8][C:9]12[CH2:17][CH2:16][CH:13]([CH2:14][CH2:15]1)[CH2:12][N:11]1[C:18](=[O:36])[C:19]([O:27][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:29])=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:21]=[C:10]21)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 57905266Ethyl 10-(benzyl(ethyl)amino)-4-oxo-3-((phenylcarbonyl)oxy)-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57904946Ethyl 10-(ethylamino)-4-oxo-3-((phenylcarbonyl)oxy)-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of ethyl 10-(benzyl(ethyl)amino)-4-oxo-3-((phenylcarbonyl)oxy)-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate (120 mg, 0.233 mmol) in methanol (5 mL) was added 1N HCl (0.256 mL, 0.256 mmol) followed by Pd/C (24.77 mg, 0.023 mmol) and the mixture stirred under 1 atm hydrogen for 18 h. The mixture was filtered and the solids thoroughly washed with dichloromethane. The filtrate was concentrated under reduced pressure and dried under high vacuum overnight to afford the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solids thoroughly washed with dichloromethane
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-f11a9c1fdb3d4a3e95dd4450e8cbde49
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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