Water → HCID 57855791, compound

HRID 475586Notes

Reaction equation

HRID 475586 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:10]2[O:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[O:18])[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].N12CCCN=[C:31]1[CH2:30][CH2:29][CH2:28][CH2:27]C2.BrCC1CCC1.O>C(O)C>[CH:28]1([CH2:27][O:1][C:2]2[CH:3]=[C:4]([C:10]3[O:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[O:18])[N:14]=3)[CH:5]=[CH:6][C:7]=2[O:8][CH3:9])[CH2:29][CH2:30][CH2:31]1

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2734658(Bromomethyl)cyclobutaneHCID 57855880HCID 57855880, compound

Product 1

HCID 57855791HCID 57855791, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 0.15 g quantity of 3-[2-(3-hydroxy-4-methoxyphenyl)oxazol-4-yl]-1-(pyridin-2-yl)propan-1-one obtained in Example 161 and 0.2 ml of 1,8-diazabicyclo[5,4,0]undec-7-ene were dissolved in 5 ml of ethanol. A 0.14 g quantity of (bromomethyl)cyclobutane was added thereto, and the mixture was heated and refluxed overnight. The reaction mixture was allowed to cool, water was then added thereto, and extraction was performed with ethyl acetate. After washing with water twice, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=5:1) to give 50 mg of white powdery 3-[2-(3-cyclobutylmethoxy-4-methoxyphenyl)oxazol-4-yl]-1-(pyridin-2-yl)propan-1-one.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed overnight
  3. temperatureto cool
  4. extractionextraction
  5. washAfter washing with water twice
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-8bda173b3b3844bba64ffd01be5689b8
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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