HCID 118222607, compound → HCID 91824203, compound

HRID 63030Notes

Reaction equation

HRID 63030 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=4)=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH:28]=1)([O-])=O>CO.C(OCC)(=O)C.[Pd]>[F:27][C:24]([F:25])([F:26])[C:21]1[CH:20]=[CH:19][C:18]([C:15]2[CH:16]=[CH:17][C:12]([C:10]3[O:11][C:7]4[CH:6]=[CH:5][C:4]([NH2:1])=[CH:28][C:8]=4[N:9]=3)=[CH:13][CH:14]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 1

HCID 118222607HCID 118222607, compound

Product 1

HCID 91824203HCID 91824203, compoundYield 54.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

27 mg (0.0703 mmol) of 5-nitro-2-(4′-trifluoromethyl-[1,1′-biphenyl]-4-yl)benzo[d]oxazole was dissolved in methanol, and then, 10% Pd/C was added thereto to allow a catalytic reaction therebetween for 4 hours under hydrogen gas atmosphere. The reaction solution was diluted with ethyl acetate. Then, the diluted reaction solution was filtered with a celite pad, and then, was concentrated under reduced pressure. Afterwards, the filtered reaction solution was purified by using a silica gel column chromatography (ethyl acetate/normal-hexane at a volume ratio of 1:1) to obtain 13.6 mg (54.6%) of 2-(4′-trifluoromethyl-[1,1′-biphenyl]-4-yl)benzo[d]oxazole-5-amine (Derivative #8).

Workup

  1. customa catalytic reaction
  2. customThen, the diluted reaction solution
  3. filtrationwas filtered with a celite pad
  4. concentrationwas concentrated under reduced pressure
  5. customAfterwards, the filtered reaction solution
  6. customwas purified

Sources & evidence

ORD record
ord-4f0e6c62f6aa4db0aeec08d30a6cb3ef
Source dataset
uspto-grants-2016_09
Patent number
US09447054B2

Reaction notes

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