HCID 118308044, compound → (1S,2S)-1-N-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine

HRID 1750496Notes

Reaction equation

HRID 1750496 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[N:14]([CH3:25])[C:15]1[CH:20]=[N:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[CH3:25][N:14]([C:15]1[CH:20]=[N:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][N:16]=1)[C@H:10]1[CH2:11][CH2:12][CH2:13][C@@H:9]1[NH2:8]

Participants

6

Reactant 2

HCID 118308044HCID 118308044, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118308113(1S,2S)-1-N-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S,2S)-1-N,1-N-dibenzyl-2-N-methyl-2-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine (285 mg, 0.647 mmol) in ethyl acetate (2 ml) and ethanol (1 ml) was added palladium on carbon (10% wt, 50% wet, 100 mg, 0.094 mmol). The resulting mixture was stirred under a balloon of hydrogen gas for 18 hours. The reaction was filtered through diatomaceous earth (commercially sold under the trade mark “Celite”) and concentrated in vacuo to afford the title compound.

Workup

  1. filtrationThe reaction was filtered through diatomaceous earth (
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05d0c9a56bf8421d8eabbca0591b0659
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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