Trifluoroacetic acid → HCID 10564438, compound

HRID 361810Notes

Reaction equation

HRID 361810 reaction equation
CC(C)(OC([N:7]1[CH2:12][CH2:11][CH:10]([N:13]([CH3:26])[C:14]2[C:19]([NH:20][C:21]([CH3:25])([CH3:24])[CH2:22][CH3:23])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=O)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl.O>[CH3:26][N:13]([CH:10]1[CH2:9][CH2:8][NH:7][CH2:12][CH2:11]1)[C:14]1[C:19]([NH:20][C:21]([CH3:24])([CH3:25])[CH2:22][CH3:23])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 10762096HCID 10762096, compound

Product 1

HCID 10564438HCID 10564438, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-[1,1-dimethylethoxycarbonyl]-4-[N-methyl-N-(3-(1,1-dimethylpropylamino)-2-pyridinyl)amino]piperidine (EXAMPLE 63, 2.39 g) in dry methylene chloride (30 ml) under nitrogen at 0° is added trifluoroacetic acid (6.37 ml) over 1 min. The resulting mixture is warmed to 20°-25°, stirred for 1.5 hrs, and then added to a mixture of sodium hydroxide (3.31 g) in water (40 ml) at 0°. The layers are separated, the aqueous phase is extracted with methylene chloride (4×40 ml), and the combined organic phases are washed with saline (40 ml), dried over sodium sulfate, and concentrated under reduced pressure to give the title compound, NMR (CDCl3) 7.66, 7.02, 6.84, 4.86, 3.39, 3.13, 2.63, 1.81-1.52, 1.31 and 0.87δ.

Workup

  1. temperatureThe resulting mixture is warmed to 20°-25°
  2. customThe layers are separated
  3. extractionthe aqueous phase is extracted with methylene chloride (4×40 ml)
  4. washthe combined organic phases are washed with saline (40 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-beabbc410a7a4158b4082b818d7bc032
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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