HCID 86670984, compound → HCID 86670985, compound

HRID 515357Notes

Reaction equation

HRID 515357 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([N:22]([C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][C:25]=3[F:33])[CH3:23])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]>C(OCC)(=O)C.[Pd]>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([N:22]([CH3:23])[CH:19]2[CH2:20][CH2:21][N:16]([CH2:15][C:12]3[CH:11]=[CH:10][C:9]([C:3]([OH:8])([C:2]([F:35])([F:1])[F:34])[C:4]([F:5])([F:6])[F:7])=[CH:14][CH:13]=3)[CH2:17][CH2:18]2)=[C:25]([F:33])[CH:26]=1

Participants

4

Reactant 1

HCID 86670984HCID 86670984, compound

Product 1

HCID 86670985HCID 86670985, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1,1,1,3,3,3-Hexafluoro-2-(4-((4-((2-fluoro-4-nitrophenyl)(methyl)amino)-piperidin-1-yl)methyl)phenyl)propan-2-ol (1.472 mmol, 750 mg) and palladium (10% on carbon, Degussa) (0.015 mmol, 31.3 mg) were hydrogenated in ethyl acetate (10 mL) at 5 bar for 1 hour at room temperature. The reaction mixture was filtered and concentrated under vacuum to give the intermediate 2-(4-((4-((4-amino-2-fluorophenyl)-(methyl)amino)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (300 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c3b8e90d626e4612853d8d81d688056c
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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