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

HRID 2282377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2282377
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-0abaf9df74244812940588bb76976b4e
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139584B2

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