Water → HCID 57855859, compound

HRID 475623Notes

Reaction equation

HRID 475623 reaction equation
[F:1][CH:2]([F:27])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]([C:19]3[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=3)=[O:18])[N:14]=2)=[CH:6][C:5]=1[OH:26].[CH2:28]1[CH2:38]CN2C(=NCCC2)C[CH2:29]1.BrC(C)C.O>C(O)C.C(OCC)(=O)C>[F:27][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]([C:19]3[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=3)=[O:18])[N:14]=2)=[CH:6][C:5]=1[O:26][CH:28]([CH3:38])[CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68984745HCID 68984745, compound

Product 1

HCID 57855859HCID 57855859, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 0.15 g quantity of the compound obtained in Example 327 and 0.18 ml of DBU were dissolved in 3 ml of ethanol, 0.15 g of 2-bromopropane was then added to the obtained solution, and heating and refluxing were conducted overnight. After cooling, water was added to the reaction mixture, and ethyl acetate extraction was performed. The organic layer was washed twice with water, concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1). The obtained crystals were recrystallized from aqueous 80% ethanol, thereby yielding 70 mg of white powdery 3-[2-(4-difluoromethoxy-3-isopropoxyphenyl)oxazol-4-yl]-1-(3-methylpyridin-2-yl)propan-1-one

Workup

  1. temperatureheating
  2. temperaturerefluxing
  3. temperatureAfter cooling
  4. washThe organic layer was washed twice with water
  5. concentrationconcentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)
  7. customThe obtained crystals were recrystallized from aqueous 80% ethanol

Sources & evidence

ORD record
ord-cbb10ab6650a4b7bb8c69b1f65d7050c
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

Loading…