Trifluoroacetic acid → 4-(2-Chloro-furo[2,3-b]pyrazin-6-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1184689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184689
FC(F)(F)C(O)=O.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]#[C:22][C:23]2[C:28](=[O:29])[N:27](CC3C=CC(OC)=CC=3)[CH:26]=[C:25]([Cl:39])[N:24]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>ClCCl.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[O:29][C:28]3=[N:27][CH:26]=[C:25]([Cl:39])[N:24]=[C:23]3[CH:22]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 679732584-[6-Chloro-4-(4-methoxy-benzyl)-3-oxo-3,4-dihydro-pyrazin-2-ylethynyl]-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 866748844-(2-Chloro-furo[2,3-b]pyrazin-6-yl)-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76223Silver(I) trifluoromethanesulfonateKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Silver triflate (6 mg) and trifluoroacetic acid (0.36 mL) are added to a solution of 4-[6-chloro-4-(4-methoxy-benzyl)-3-oxo-3,4-dihydro-pyrazin-2-ylethynyl]-piperidine-1-carboxylic acid tert-butyl ester (430 mg) in dichloromethane (6 mL). The reaction mixture is stirred at room temperature for 20 min, diluted with dichloromethane and washed with aqueous NaHCO3 solution and brine. The organic phase is dried (MgSO4) and the solvent is evaporated. The residue is chromatographed on silica gel (ethyl acetate/cyclohexane 25:70) to give the title compound as a colorless solid.

Aufarbeitung

  1. washwashed with aqueous NaHCO3 solution and brine
  2. dry with materialThe organic phase is dried (MgSO4)
  3. customthe solvent is evaporated
  4. customThe residue is chromatographed on silica gel (ethyl acetate/cyclohexane 25:70)

Quellen und Nachweise

ORD-Eintrag
ord-983338dc71b24cc09513523ac1c366d8
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669271B2

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