Hydrochloric Acid → 1-[2-(1-Adamantyl)ethyl]-1-hydroxy-3-[3-(4-pyridyl)propyl]urea

HRID 1393177Notes

Reaction equation

HRID 1393177 reaction equation
Cl.[C:2]12([CH2:12][CH2:13][N:14]([O:27]CC3C=CC=CC=3)[C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[O:16])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2>>[C:2]12([CH2:12][CH2:13][N:14]([OH:27])[C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[O:16])[CH2:9][CH:8]3[CH2:7][CH:6]([CH2:5][CH:4]([CH2:10]3)[CH2:3]1)[CH2:11]2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 219739741-[2-(1-Adamantyl)ethyl]-1-benzyloxy-3-[3-(4-pyridyl)propyl]urea

Product 1

HCID 219740551-[2-(1-Adamantyl)ethyl]-1-hydroxy-3-[3-(4-pyridyl)propyl]ureaYield 34%

Procedure

2 N Hydrochloric acid (4.0 ml) was added to a solution of 1-[2-(1-adamantyl)ethyl]-1-benzyloxy-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-28) (438 mg, 0.978 mmol) in methanol (9.78 ml), and a nitrogen gas was bubbled through the mixture. To the mixture was added 10% palladium on carbon (43 mg), and the whole was stirred under hydrogen at 1 atm for three days. The palladium on carbon was filtered out, the filtrate was concentrated under reduced pressure, and the concentrate was diluted with diethyl ether (30 ml). The whole was washed with a saturated aqueous sodium hydrogencarbonate solution (30 ml) and a saturated aqueous sodium chloride solution (30 ml) successively, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give 119 mg (34%) of the titled compound.

Workup

  1. custom1-28) (438 mg, 0.978 mmol) in methanol (9.78 ml), and a nitrogen gas was bubbled through the mixture
  2. additionTo the mixture was added 10% palladium on carbon (43 mg)
  3. filtrationThe palladium on carbon was filtered out
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionthe concentrate was diluted with diethyl ether (30 ml)
  6. washThe whole was washed with a saturated aqueous sodium hydrogencarbonate solution (30 ml)
  7. dry with materiala saturated aqueous sodium chloride solution (30 ml) successively, and the organic layer was dried over magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dc0bc14471f44bf98f9cf7d48bc77116
Source dataset
uspto-grants-2008_03
Patent number
US07345064B2

Reaction notes

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