Trifluoroacetic acid → 2-(3-Piperidin-4-ylmethyl-[1,2,4]oxadiazol-5-yl)furo[3,2-c]pyridine

HRID 217172

Reaktionsgleichung

Reaktionsgleichung von HRID 217172
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]2[N:26]=[C:25]([C:27]3[O:35][C:34]4[CH:33]=[CH:32][N:31]=[CH:30][C:29]=4[CH:28]=3)[O:24][N:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]2[N:26]=[C:25]([C:27]3[O:35][C:34]4[CH:33]=[CH:32][N:31]=[CH:30][C:29]=4[CH:28]=3)[O:24][N:23]=2)[CH2:17][CH2:16]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 576595624-(5-Furo[3,2-c]pyridin-2-yl-[1,2,4]oxadiazol-3-ylmethyl)piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 116305842-(3-Piperidin-4-ylmethyl-[1,2,4]oxadiazol-5-yl)furo[3,2-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TFA (10 mL) was added to a stirred solution of 4-(5-furo[3,2-c]pyridin-2-yl-[1,2,4]oxadiazol-3-ylmethyl)piperidine-1-carboxylic acid tert-butyl ester (Example 44, 1.76 g, 4.56 mmol) in anhydrous CH2Cl2 (20 mL). After 1 h, the solvents were removed under reduced pressure. The residue was taken up in CH2Cl-MeOH (9:1, 100 mL), before being washed with 2M NaOH (100 mL). The aqueous phase was extracted with CH2Cl2-MeOH (9:1, 2×100 mL), then the organic extracts were combined, dried (MgSO4), and concentrated to furnish the title compound: m/z (ES+)=285.0 [M+H]+.

Aufarbeitung

  1. customthe solvents were removed under reduced pressure
  2. washbefore being washed with 2M NaOH (100 mL)
  3. extractionThe aqueous phase was extracted with CH2Cl2-MeOH (9:1, 2×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-de6df570550149789450fbf124e1e1c2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193359B2

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