Acetic Anhydride → HCID 12136650, compound

HRID 1393175Notes

Reaction equation

HRID 1393175 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.Cl.Cl.[C:10]12([CH2:20][CH2:21][N:22]([NH2:35])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)=[O:24])[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2>N1C=CC=CC=1>[C:5]([NH:35][N:22]([CH2:21][CH2:20][C:10]12[CH2:11][CH:12]3[CH2:18][CH:16]([CH2:15][CH:14]([CH2:13]3)[CH2:19]1)[CH2:17]2)[C:23]([NH:25][CH2:26][CH2:27][CH2:28][C:29]1[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=1)=[O:24])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 219740351-[2-(1-Adamantyl)ethyl]-1-amino-3-[3-(4-pyridyl)propyl]urea dihydrochloride

Product 1

HCID 12136650HCID 12136650, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Pyridine (2.0 ml) and acetic anhydride (1.0 ml) were added to 1-[2-(1-adamantyl)ethyl]-1-amino-3-[3-(4-pyridyl)propyl]urea dihydrochloride (Compound No. 3-3) (0.20 g, 0.47 mmol) at room temperature, and the mixture was stirred for 15 minutes. The solvent was evaporated under reduced pressure from the reaction mixture, and the residue was distributed with ethyl acetate (10 ml) and water (10 ml). The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution (10 ml) and saturated brine (10 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatographyto give 0.11 g (58%) of the titled compound.

Workup

  1. customThe solvent was evaporated under reduced pressure from the reaction mixture
  2. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution (10 ml) and saturated brine (10 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatographyto

Sources & evidence

ORD record
ord-bd64d3863d7f448a9c7445c5563a47f0
Source dataset
uspto-grants-2008_03
Patent number
US07345064B2

Reaction notes

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