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 1750543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750543
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d3de7360ee4b4da19541affa4c6937fc
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156829B2

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