6-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate → 1,1-dimethylethyl {(2S,3R)-3-hydroxy-8-[6-(methyloxy)-1,5-naphthyridin-4-yl]-8-azaspiro[4.5]dec-2-yl}carbamate

HRID 734229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734229
[OH:1][CH:2]1[CH2:6][C:5]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:4][CH:3]1[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].FC(F)(F)S(O[C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[N:34]=2)[N:29]=[CH:28][CH:27]=1)(=O)=O>CN(C=O)C>[OH:1][C@@H:2]1[CH2:6][C:5]2([CH2:11][CH2:10][N:9]([C:26]3[C:35]4[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[N:34]=4)[N:29]=[CH:28][CH:27]=3)[CH2:8][CH2:7]2)[CH2:4][C@@H:3]1[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17]

Komponenten

4

Edukt 2

HCID 112552656-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonateHCID 765808691,1-Dimethylethyl (3-hydroxy-8-azaspiro[4.5]dec-2-yl)carbamate

Produkt 1

HCID 578429321,1-dimethylethyl {(2S,3R)-3-hydroxy-8-[6-(methyloxy)-1,5-naphthyridin-4-yl]-8-azaspiro[4.5]dec-2-yl}carbamateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1,1-dimethylethyl (3-hydroxy-8-azaspiro[4.5]dec-2-yl)carbamate (185 mg, 0.685 mmol) and 6-(methyloxy)-1,5-naphthyridin-4-yl trifluoromethanesulfonate (211 mg, 0.685 mmol) in DMF (1 mL) were stirred at 90° C. After 12 h, the solution was concentrated and the residue purified via column chromatography (silica, 1-2% MeOH in DCM (1% NH4OH)) yielding the title compound (220 mg, 75%) as a white foam: LCMS (ES) m/e 430 (M+H)+.

Aufarbeitung

  1. concentrationthe solution was concentrated
  2. customthe residue purified via column chromatography (silica, 1-2% MeOH in DCM (1% NH4OH))

Quellen und Nachweise

ORD-Eintrag
ord-ff46ea13b64143529f1e54847c2dfe69
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592334B2

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