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

HRID 639102

Reaktionsgleichung

Reaktionsgleichung von HRID 639102
[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].[F: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]([F: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 86616799(+/-)-Phenylmethyl {[cis-4-fluoro-3-pyrrolidinyl]methyl}carbamate

Produkt 1

HCID 131728031(+/-)-Phenylmethyl[(cis-4-fluoro-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamateAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 8-ethenyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine (0.26 g, 1.28 mmole) in EtOH (5 mL) was added (±)-phenylmethyl {[cis-4-fluoro-3-pyrrolidinyl]methyl}carbamate (0.32 g, 1.28 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 (0.20 g, 34%) as a light yellow foam: LC-MS (ES) m/e 457 (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-4d0853b8c75848bbaabb4e610a66aac7
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691850B2

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