Trifluoroacetic acid → N-[4-((1S,4S)-4-Amino-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-pyridin-2-yl]-2-methoxy-acetamide

HRID 1402102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1402102
C(OC(=O)[NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26](=[O:30])[CH2:27][O:28][CH3:29])[CH:20]=2)[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH3:7].[NH2:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26](=[O:30])[CH2:27][O:28][CH3:29])[CH:20]=2)[CH2:10][CH2:9]1

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86686965{(1S,4S)-4-[2-(2-Methoxy-acetylamino)-pyridin-4-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-carbamic acid tert-butyl ester

Produkt 2

HCID 222AmmoniaHCID 86686966N-[4-((1S,4S)-4-Amino-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-pyridin-2-yl]-2-methoxy-acetamideAusbeute 198,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of Intermediate 10c (272 mg, 0.64 mmol) in DCM (6 mL) was added TFA (2 mL), and the mixture stirred at RT for 30 min. The mixture was concentrated in vacuo. The residue was purified on an Isolute SCX-2 cartridge, eluting with MeOH then 0.4-1M NH3 in MeOH, to give the title compound as a colourless gum (208 mg, 100%). LCMS (Method 3): Rt 0.44 min, m/z 350.2 [MNa+].

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified on an Isolute SCX-2 cartridge
  3. washeluting with MeOH

Quellen und Nachweise

ORD-Eintrag
ord-568771932ea8412fb3804545035077c9
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907094B2

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