HCID 22288621, compound → HCID 22288624, compound

HRID 968274Notes

Reaction equation

HRID 968274 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[CH2:16][CH2:17][C:18]2[O:19][C:20]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[F:31])=[N:21][N:22]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[NH:23][C:20]1[O:19][C:18]([CH2:17][CH2:16][C:15]([NH:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:32])=[N:22][N:21]=1

Participants

4

Reactant 1

HCID 22288621HCID 22288621, compound

Product 1

HCID 22288624HCID 22288624, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(1-Benzylpiperidin-4-yl)-3-{5-[(2,4-difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}propanamide (8.14 g, 18.4 mmol) was dissolved in ethanol and hydrogenated over a Pd/C catalyst at 3 bar until the reaction had gone to completion. The reaction mixture was filtered and the filtrate was evaporated to dryness, leaving an off-white solid which was triturated in ether, filtered and then dried in air to leave the subtitle compound (2.68 g, 41%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. customleaving an off-white solid which
  4. customwas triturated in ether
  5. filtrationfiltered
  6. customdried in air

Sources & evidence

ORD record
ord-cd10d8ce1821470abcfcec3da5442c9e
Source dataset
uspto-grants-2005_10
Patent number
US06958350B2

Reaction notes

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