Ethyl Acetate → tert-butyl 1-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)pyrrolidin-3-ylcarbamate

HRID 1969533

Reaktionsgleichung

Reaktionsgleichung von HRID 1969533
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH2:20][NH:21][C:22]([N:24]3[CH2:28][CH2:27][CH:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25]3)=S)[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+].CCOC(C)=O>C1COCC1.FC(F)(F)C([O-])=O.[Hg+2].FC(F)(F)C([O-])=O>[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:22]([N:24]4[CH2:28][CH2:27][CH:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25]4)=[N:21][CH:20]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 58558007tert-butyl 1-((5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methylcarbamothioyl)pyrrolidin-3-ylcarbamate

Produkt 1

HCID 67998161tert-butyl 1-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)pyrrolidin-3-ylcarbamateAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2723924Mercury bis(trifluoroacetate)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 1-((5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methylcarbamothioyl)-pyrrolidin-3-ylcarbamate (0.54 g, 1.0 mmol, Preparation #J.1) in THF (15 mL) was added DIEA (0.444 mL, 2.54 mmol) followed by mercury (II) trifluoroacetate (0.478 g, 1.12 mmol). The reaction mixture was stirred at ambient temperature for about 2 h and then saturated aqueous NaHCO3 (30 mL) and EtOAc (30 mL) were added. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concd in vacuo. The crude material was purified by chromatography on silica gel (40 g) eluting with 10-40% EtOAc in DCM to provide tert-butyl 1-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)pyrrolidin-3-ylcarbamate (0.411 g, 81%) as a yellow glass: LC/MS (Table 1, Method a) Rt=2.50 min; MS m/z: 497 (M+H)+.

Aufarbeitung

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customThe crude material was purified by chromatography on silica gel (40 g)
  5. washeluting with 10-40% EtOAc in DCM

Quellen und Nachweise

ORD-Eintrag
ord-cd15607c98984245835ec91f8b2d50cc
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

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