Water → HCID 25142154, compound

HRID 475636Notes

Reaction equation

HRID 475636 reaction equation
[F:1][CH:2]([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:12]=[C:13]([CH2:15][NH:16][C:17](=[O:27])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH2:25][CH3:26])[N:14]=2)=[CH:6][C:5]=1[OH:28].C1CCN2C(=NCCC2)CC1.[CH2:41](Br)[CH:42]([CH3:44])[CH3:43].O>C(O)C.C(OCC)(=O)C>[F:29][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][NH:16][C:17](=[O:27])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH2:25][CH3:26])[N:14]=2)=[CH:6][C:5]=1[O:28][CH2:41][CH:42]([CH3:44])[CH3:43]

Participants

7

Reactant 4

HCID 962WaterHCID 65551-Bromo-2-methylpropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68983382HCID 68983382, compound

Product 1

HCID 25142154HCID 25142154, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 80 mg quantity of the compound obtained in Example 347 and 0.1 ml of DBU were dissolved in 2 ml of ethanol, 80 mg of isobutyl bromide was then added to the obtained solution, and heating and refluxing were conducted overnight. After cooling, water was added to the obtained 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 30 mg of white powdery N-[2-(4-difluoromethoxy-3-isobutoxyphenyl)oxazol-4-ylmethyl]-2-ethoxybenzamide.

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-909d8620acb746088b2a5c66fcd1459c
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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