8-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridine → (+/-)-Phenylmethyl[(trans-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]carbamate

HRID 639087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639087
[CH:1]([C:3]1[C:4]([F:15])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[CH:8]2)=[CH2:2].[OH:16][C@@H:17]1[CH2:21][NH:20][CH2:19][C@H:18]1[CH2:22][NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCO>[C:27]1([CH2:26][O:25][C:24](=[O:33])[NH:23][CH2:22][C@H:18]2[C@H:17]([OH:16])[CH2:21][N:20]([CH2:2][CH2:1][C:3]3[C:12]4[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[N:11]=4)[N:6]=[CH:5][C:4]=3[F:15])[CH2:19]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

4

Edukt 2

HCID 575995778-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridineHCID 86616792(+/-)-Phenylmethyl {[trans-4-hydroxy-3-pyrrolidinyl]methyl}carbamate

Produkt 1

HCID 131728028(+/-)-Phenylmethyl[(trans-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]carbamateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 8-ethenyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine (2.55 g, 12.5 mmole) in EtOH (10 mL) was added phenylmethyl(±)-{[trans-4-hydroxy-3-pyrrolidinyl]methyl}carbamate (3.12 g, 12.5 mmole). After 24 h at 80° C. the reaction contents were purified on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) affording the title compound (5.56 g, 98%) as a light yellow foam: LC-MS (ES) m/e 455 (M+H)+.

Aufarbeitung

  1. customAfter 24 h at 80° C. the reaction contents
  2. customwere purified on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-74ef9c0cecea42e1b41b9aaf9102893d
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691850B2

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