N,N-Dimethylethylenediamine → 1-Chloro-N-(2-(dimethylamino)ethyl)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-9-carboxamide

HRID 1029237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1029237
[Cl:1][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([C:17]([OH:19])=O)[CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.CCN(C(C)C)C(C)C.[CH:29]1[N:33]=[CH:32][N:31]([C:34](N2C=NC=C2)=O)[CH:30]=1.CN(C)CCN>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([C:17]([NH:33][CH2:29][CH2:30][N:31]([CH3:34])[CH3:32])=[O:19])[CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2

Komponenten

6

Edukt 4

HCID 66053N,N-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 581681651-Chloro-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-9-carboxylic acid

Produkt 1

HCID 698106731-Chloro-N-(2-(dimethylamino)ethyl)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-9-carboxamideAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

295 (60 mg, 0.22 mol), DIEA (0.08 mL, 0.44 mmol), and CDI (71 mg, 0.44 mmol) were suspended in DMF (2 mL) and stirred for 4 h at room temperature. N1,N1-Dimethylethane-1,2-diamine (77 mg, 0.87 mmol) was added, and the reaction mixture was stirred for another 3 h. The reaction mixture was quenched with water. The resulting precipitate was filtered, washed with MeOH and H2O, and dried under vacuum to produce provide 296 (61 mg, 81% yield) as a solid. LC-MS (M+H=345, obsd.=345).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for another 3 h
  2. customThe reaction mixture was quenched with water
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with MeOH and H2O
  5. customdried under vacuum
  6. customto produce

Quellen und Nachweise

ORD-Eintrag
ord-63040a6a2c044a11ac5d27327c365570
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735584B2

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