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Water → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 4-diisopropylaminobutyrate

HRID 1029498
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1029498
N12CCCN=C1CCCCC2.Cl[CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[N:26][C:27]([Cl:33])=[CH:28][CH:29]=2)[N:24]=1.Cl.[CH:35]([N:38]([CH:45]([CH3:47])[CH3:46])[CH2:39][CH2:40][CH2:41][C:42]([OH:44])=[O:43])([CH3:37])[CH3:36].O>CN(C)C=O.C(Cl)Cl>[CH:45]([N:38]([CH:35]([CH3:37])[CH3:36])[CH2:39][CH2:40][CH2:41][C:42]([O:44][CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[N:26][C:27]([Cl:33])=[CH:28][CH:29]=2)[N:24]=1)=[O:43])([CH3:47])[CH3:46]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinoneHCID 867456314-Diisopropylaminobutyric acid hydrochloride

Produkt 1

HCID 867456302-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 4-diisopropylaminobutyrateAusbeute 49,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

1,8-Diazabicyclo[5.4.0]undec-7-ene (10.7 g) is added dropwise to a suspension of 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (9.9 g) and 4-diisopropylaminobutyric acid hydrochloride (6.7 g) in dimethylformamide (100 cc), and the mixture is stirred at a temperature in the region of 20° C. for 20 hours. The reaction mixture is then poured into water (130 cc). The solid obtained is separated by filtration and then dissolved in methylene chloride (200 cc). The organic extracts are washed with 0.1 N aqueous hydrochloric acid solution (2×35 cc), 0.5 N aqueous hydrochloric acid solution (35 cc), and then with water (2×35 cc). The organic phase is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is taken up with methylene chloride (200 cc). The organic phase is washed with saturated aqueous sodium hydrogen carbonate solution (2×50 cc). The organic phase is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized in isopropyl ether. 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 4-diisopropylaminobutyrate (7.1 g), m.p. 118° C., is thereby obtained.

Aufarbeitung

  1. customThe solid obtained
  2. customis separated by filtration
  3. dissolutiondissolved in methylene chloride (200 cc)
  4. washThe organic extracts are washed with 0.1 N aqueous hydrochloric acid solution (2×35 cc), 0.5 N aqueous hydrochloric acid solution (35 cc)
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. customThe residue obtained
  9. washThe organic phase is washed with saturated aqueous sodium hydrogen carbonate solution (2×50 cc)
  10. dry with materialThe organic phase is dried over magnesium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  13. customThe residue is recrystallized in isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f374675e541843e2856edee1bce806f5
Quelldatensatz
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05102890

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