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

HRID 11473Notes

Reaction equation

HRID 11473 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-fb48d7daa0574f5e892827858802681b
Source dataset
uspto-grants-2006_08
Patent number
US07098226B2

Reaction notes

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