HCID 67121204, compound → HCID 25182301, compound

HRID 1510455Notes

Reaction equation

HRID 1510455 reaction equation
[CH:1]1([NH:6][C:7]([C:9]2[C:13]([CH:14]=[CH2:15])=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[O:11][N:10]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[CH:1]1([NH:6][C:7]([C:9]2[C:13]([CH2:14][CH3:15])=[C:12]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:20][CH:21]=3)[O:11][N:10]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 67121204HCID 67121204, compound

Product 1

HCID 25182301HCID 25182301, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of N-cyclopentyl-5-(4-(trifluoromethyl)phenyl)-4-vinylisoxazole-3-carboxamide (70 mg, 0.2 mmol) in ethanol (2 mL), palladium on carbon (5%) (5 mg) was added and the reaction mixture was then placed under a hydrogen atmosphere (balloon) for 2 hours. After this time the crude mixture was filtered through celite and concentrated in vacuo. Purification by silica gel chromatography eluting with heptane increasing to heptane to 15% ethylacetate in heptane afforded the title compound (36 mg, 0.1 mmol).

Workup

  1. customfor 2 hours
  2. filtrationAfter this time the crude mixture was filtered through celite and
  3. concentrationconcentrated in vacuo
  4. customPurification by silica gel chromatography
  5. washeluting with heptane increasing to heptane to 15% ethylacetate in heptane

Sources & evidence

ORD record
ord-7abb436ebb7f4b7c829cee2419ce5cdc
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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