8-Ethenyl-2-methoxy-1,5-naphthyridine → phenylmethyl[((3S,4S)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate

HRID 639117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639117
[CH:1]([C:3]1[CH:4]=[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:15][C@@H:16]1[CH2:20][NH:19][CH2:18][C@@H:17]1[CH2:21][NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CCO>[C:26]1([CH2:25][O:24][C:23](=[O:32])[NH:22][CH2:21][C@@H:17]2[C@H:16]([OH:15])[CH2:20][N:19]([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][CH:4]=3)[CH2:18]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

4

Edukt 2

HCID 575995738-Ethenyl-2-methoxy-1,5-naphthyridineHCID 59026130Phenylmethyl {[(3R,4S)-4-hydroxy-3-pyrrolidinyl]methyl}carbamate

Produkt 1

HCID 59026158phenylmethyl[((3S,4S)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 8-ethenyl-2-(methyloxy)-1,5-naphthyridine (4.2 mmole) in EtOH (5 mL) was added phenylmethyl {[(3R,4S)-4-hydroxy-3-pyrrolidinyl]methyl}carbamate (1.05 g, 4.2 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 (1.46 g, 80%) as a light yellow foam: LC-MS (ES) m/e 437 (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-922c595f5924440b92fcaa709b45917e
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691850B2

Notizen zur Reaktion

Wird geladen…