Triethylamine → HCID 484993, Verbindung

HRID 1861803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1861803
Cl.[Br:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].C(N(CC)CC)C.[N:18]1[C:27]2[C:22](=[CH:23][N:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[C:28](O)=[O:29].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.CCOC(C)=O>[Br:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:28]([C:19]1[CH:20]=[CH:21][C:22]2[C:27](=[CH:26][CH:25]=[N:24][CH:23]=2)[N:18]=1)=[O:29]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27242022-Bromobenzylamine hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 484993HCID 484993, VerbindungAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a stirring solution of 2-bromobenzylamine hydrochloride (80.7 mg, 95%, 0.345 mmol) in anhydrous DMF (5 ml) was added triethylamine (51.8 ul. 0.345 mmol), After 5 min, 2-[1,6]naphthyridinecarboxylic acid (40 mg, 0.229 mmol), 1-hydroxybenzotriazole hydrate (34.2 mg, 0.253 mmol) and 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (48.5 mg, 0.253 mmol) was sequentially added. The resulting mixture was allowed to stir at room temperature for 4 h and it was found to be clear. The solvent was removed under vacuum and the resulting residue was redissolved in CH2Cl2 (100 ml). The organic layer was washed with aqueous NaHCO3, dried over anhydrous MgSO4, and concentrated to give the crude mixture. Chromatography of the crude (Hex:EtOAc=1:1 to pure EtOAc) afforded desired product as white solid (70 mg, 89%): m.p. 129-130° C.

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. dissolutionthe resulting residue was redissolved in CH2Cl2 (100 ml)
  3. washThe organic layer was washed with aqueous NaHCO3
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customto give the crude mixture

Quellen und Nachweise

ORD-Eintrag
ord-8aaf9897f7224edcbdf52cb3294ea829
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06534520B2

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