HCID 44603390, compound → HCID 44603391, compound

HRID 2363200Notes

Reaction equation

HRID 2363200 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[O:20][C:21]([C:24]3[CH:29]=[C:28]([CH:30]=[CH2:31])[CH:27]=[C:26]([C:32]([F:35])([F:34])[F:33])[CH:25]=3)=[CH:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[H][H]>CCO.CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[O:20][C:21]([C:24]3[CH:25]=[C:26]([C:32]([F:35])([F:33])[F:34])[CH:27]=[C:28]([CH2:30][CH3:31])[CH:29]=3)=[CH:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:10])=[O:11]

Participants

6

Reactant 2

HCID 44603390HCID 44603390, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44603391HCID 44603391, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of example 114 compound (20 mg, 0.04 mmol) and 10% Pd—C (10 mg) in EtOH was hydrogenated using hydrogen balloon for 2 hours. The mixture was diluted with EtOAc, filtered through silica gel pad and washed with EtOAc. The filtrate was concentrated under reduced pressure to give the title compound (5 mg, 24%) after recrystallization with EtOAc/Hex.

Workup

  1. customfor 2 hours
  2. filtrationfiltered through silica gel pad
  3. washwashed with EtOAc
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5ffb655101aa439eb29772dd021f68f0
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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