Triethylamine → 7-(1-[(N-acetyl)aminomethyl]-3-azabicyclo[3.1.0]-hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester

HRID 484209

Reaktionsgleichung

Reaktionsgleichung von HRID 484209
[C:1]([NH:4][CH2:5][C:6]12[CH2:11][CH:10]1[CH2:9][NH:8][CH2:7]2)(=[O:3])[CH3:2].[CH2:12](N(CC)CC)[CH3:13].Cl[C:20]1[N:29]=[C:28]2[C:23]([C:24](=[O:41])[C:25]([C:38]([OH:40])=[O:39])=[CH:26][N:27]2[C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=2[F:37])=[CH:22][C:21]=1[F:42].N1C2C(=CC=CN=2)C=CC=1>C(#N)C>[C:1]([NH:4][CH2:5][C:6]12[CH2:11][CH:10]1[CH2:9][N:8]([C:20]1[N:29]=[C:28]3[C:23]([C:24](=[O:41])[C:25]([C:38]([O:40][CH2:12][CH3:13])=[O:39])=[CH:26][N:27]3[C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=3[F:37])=[CH:22][C:21]=1[F:42])[CH2:7]2)(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 1360691,8-NaphthyridineHCID 105460847-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 157134281-[(N-acetyl)aminomethyl]-3-azabicyclo[3.1.0]hexane

Produkt 1

HCID 157134527-(1-[(N-acetyl)aminomethyl]-3-azabicyclo[3.1.0]-hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 1-[(N-acetyl)aminomethyl]-3-azabicyclo[3.1.0]hexane (115.5 mg, 0.75 mmol) and triethylamine (312 μl, 2.25 mmol) in acetonitrile (20 ml) was treated with the ethyl ester of 7-chloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (283 mg, 0.74 mmol) and heated to 80° for 20 hours. Additional 1-(N-acetyl)-aminomethyl-3-azabicyclo[3.1.0]hexane (97 mg) was added portionwise over 2.5 hours until thin layer chromatography indicated the absence of starting naphthyridine. The reaction mixture was concentrated in vacuo, and the residue chromatographed on silica gel (eluant: 189:10:1 chloroform:methanol:concentrated ammonium hydroxide). The title product was obtained as a colorless oil (280.3 mg, 0.56 mmol, 76% yield).

Aufarbeitung

  1. temperatureheated to 80° for 20 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue chromatographed on silica gel (eluant: 189:10:1 chloroform:methanol:concentrated ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-4379bc3efa324452b4604ab1434bf3a5
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05229396

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