Phenylmethyl[(3s)-3-pyrrolidinylmethyl]carbamate → phenylmethyl[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate

HRID 639069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639069
[C:1]1([CH2:7][O:8][C:9](=[O:17])[NH:10][CH2:11][C@H:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18]([C:20]1[C:21]([F:32])=[CH:22][N:23]=[C:24]2[C:29]=1[N:28]=[C:27]([O:30][CH3:31])[CH:26]=[CH:25]2)=[CH2:19]>CN(C=O)C>[C:1]1([CH2:7][O:8][C:9](=[O:17])[NH:10][CH2:11][C@@H:12]2[CH2:16][CH2:15][N:14]([CH2:19][CH2:18][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[N:28]=4)[N:23]=[CH:22][C:21]=3[F:32])[CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 45072662Phenylmethyl[(3s)-3-pyrrolidinylmethyl]carbamateHCID 575995778-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridine

Produkt 1

HCID 59026091phenylmethyl[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of phenylmethyl[(3S)-3-pyrrolidinylmethyl]carbamate (127 mg, 0.54 mmole) in DMF (1 mL) was added 8-ethenyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine (0.10 g, 0.49 mmole). After 24 h at 100° C., the reaction contents were purified on silica gel (CHCl3/MeOH, 9:1, containing 5% NH4OH) to afford the title compound (0.16 g, 77%) as a light yellow oil: LC-MS (ES) m/e 439 (M+H)+.

Aufarbeitung

  1. customthe reaction contents
  2. customwere purified on silica gel (CHCl3/MeOH, 9:1, containing 5% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-08cad5d4eb1a4324a94fdf88e9eebdcd
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691850B2

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