tert-butyl ((1S,2S)-2-((5-(trifluoromethyl)-3-vinylpyrazin-2-yl)amino)cyclopentyl)carbamate → tert-butyl ((1S,2S)-2-((3-ethyl-5-(trifluoromethyl)pyrazin-2-yl)amino)cyclopentyl)carbamate

HRID 1750543Notes

Reaction equation

HRID 1750543 reaction equation
[CH:1]([C:3]1[C:4]([NH:13][C@H:14]2[CH2:18][CH2:17][CH2:16][C@@H:15]2[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:8]=1)=[CH2:2].[H][H]>CO.[Pd]>[CH2:1]([C:3]1[C:4]([NH:13][C@H:14]2[CH2:18][CH2:17][CH2:16][C@@H:15]2[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[N:5][CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[N:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 118308332tert-butyl ((1S,2S)-2-((5-(trifluoromethyl)-3-vinylpyrazin-2-yl)amino)cyclopentyl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 118308096tert-butyl ((1S,2S)-2-((3-ethyl-5-(trifluoromethyl)pyrazin-2-yl)amino)cyclopentyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl N-[(1S,2S)-2-{[3-ethenyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]carbamate (460 mg, 1.24 mmol) in methanol (12 ml) was added palladium on carbon (10% wt, 50% wet) (131 mg, 0.124 mmol) and the resulting mixture was stirred under a balloon of hydrogen gas for 2 hours. The reaction was filtered through diatomaceous earth (commercially sold under the trade mark “Celite”). To this was then added further palladium on carbon (10% wt, 50% wet) (131 mg, 0.124 mmol) and the resulting mixture was stirred under a balloon of hydrogen gas for 72 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. additionTo this was then added further palladium on carbon (10% wt
  3. filtrationThe reaction was filtered through diatomaceous earth (
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3de7360ee4b4da19541affa4c6937fc
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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