Triethylamine → N-[(3-bromophenyl)methyl]-1,6-naphthyridine-2-carboxamide

HRID 1383404

Reaktionsgleichung

Reaktionsgleichung von HRID 1383404
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].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:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH:7][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 27249803-Bromobenzylamine hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 484994N-[(3-bromophenyl)methyl]-1,6-naphthyridine-2-carboxamideAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a stirring solution of 3-bromobenzylamine hydrochloride (77.5 mg, 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-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (48.5 mg, 0.253 mmol) was sequentially added. The resulting mixture was allowed to stir at room temperature overnight 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 (64 mg, 81%): m.p. 112-113° 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-d29659b9ccf444a79f677a8331ec94a9
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255318B1

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