Water → 1-[2-(Acetylamino)ethyl]-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2364346
[NH2:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][O:28][CH2:29][CH3:30])=[O:24])[C:5]1=[O:31].C(N(C(C)C)CC)(C)C.[C:41](OC(=O)C)(=[O:43])[CH3:42].O>CN(C=O)C>[C:41]([NH:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][O:28][CH2:29][CH3:30])=[O:24])[C:5]1=[O:31])(=[O:43])[CH3:42]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 694808831-(2-Aminoethyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Produkt 1

HCID 867623221-[2-(Acetylamino)ethyl]-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1-(2-aminoethyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.020 g, 0.047 mmol) and diisopropyl ethylamine (0.041 mL, 0.24 mmol) in DMF (5 mL) under nitrogen was treated with acetic anhydride (0.0044 mL, 0.047 mmol) at ambient temperature. The reaction was warmed slightly to solubilize the reacted at ambient temperature for 10 min. Water was added (2 mL) and the reaction was cooled to 0° C. and concentrated in vacuo. The resulting residue was treated with 1 N NaHSO4 and filtered then triturated with Et2O and dried in vacuo to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 1.1 (t, J=6.9 Hz, 3 H), 1.7 (s, 3 H), 3.3 (dd, J=12.5, 5.3 Hz, 2 H), 3.5 (q, J=7.0 Hz, 2 H), 3.5 (s, 4 H), 4.1 (s, 2 H), 4.3 (t, J=6.7 Hz, 2 H), 7.1 (t, J=9.0 Hz, 2 H), 7.4 (dd, J=8.4, 5.5 Hz, 2 H), 8.0 (t, J=5.6 Hz, 1 H), 8.2 (s, 1 H), 8.6 (s, 1 H), 10.4 (s, 1 H), 17.1 (s, 1 H); ES+ MS: 471 (M+H+).

Aufarbeitung

  1. temperatureThe reaction was warmed slightly
  2. customreacted at ambient temperature for 10 min
  3. concentrationconcentrated in vacuo
  4. additionThe resulting residue was treated with 1 N NaHSO4
  5. filtrationfiltered
  6. customthen triturated with Et2O
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1b771a78ad724b98bafdf0159c1d3d06
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691991B2

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