HCID 86725351, compound → HCID 86725352, compound

HRID 925243Notes

Reaction equation

HRID 925243 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([N:5]1[CH2:23][CH2:22][C:9]2[C:10]3[C:11]([C:17]4[S:18][CH:19]=[CH:20][N:21]=4)=[CH:12][CH2:13][C:14]=3[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[H][H]>C(O)C.[Pd]>[F:25][C:2]([F:1])([F:24])[C:3]([N:5]1[CH2:23][CH2:22][C:9]2[C:10]3[CH:11]([C:17]4[S:18][CH:19]=[CH:20][N:21]=4)[CH2:12][CH2:13][C:14]=3[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 86725351HCID 86725351, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86725352HCID 86725352, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product from step (c) (22 mg) was dissolved in ethanol (30 ml) placed in a Parr Hydrogenation bottle. To this solution was added 10% Pd—C (100 mg). The mixture was shaken at 50° C. over 50 psi of hydrogen for 16 hours. The reaction mixture was purged with Nitrogen, cooled to RT, and filtered thru a pad of celite. The solvent was evaporated in vacuo to give the crude product as a light yellow oil. Purification by flash silica-gel chromatography (gradient elution: 0-50% EtOAc in hexanes) gave the sub-title compound (17 mg) as a white film. MS: ESI (positive): 367 (M+H).

Workup

  1. customThe reaction mixture was purged with Nitrogen
  2. filtrationfiltered
  3. customThe solvent was evaporated in vacuo
  4. customto give the crude product as a light yellow oil
  5. customPurification
  6. washby flash silica-gel chromatography (gradient elution: 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e06fe4ad657b4d11b27eec4e38a2b6cb
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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