Diisopropyl Ether → HCID 22754726, Verbindung

HRID 2083736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2083736
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[N:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([N:18]3[CH:26]([O:27]C(OC4C=CC=CC=4)=O)[C:25]4[C:20](=[N:21][CH:22]=[CH:23][N:24]=4)[C:19]3=[O:37])=[N:15]2)=[CH:10][CH:9]=1.[CH:38]([O:41]C(C)C)(C)C>CN(C)C=O>[Cl:7][C:8]1[N:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([N:18]3[CH:26]([O:27][C:38]([N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[O:41])[C:25]4[C:20](=[N:21][CH:22]=[CH:23][N:24]=4)[C:19]3=[O:37])=[N:15]2)=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 7914Diisopropyl EtherHCID 8082PiperidineHCID 233436456-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-5-phenoxycarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine

Produkt 1

HCID 22754726HCID 22754726, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of piperidine (3.06 g.) in anhydrous dimethylformamide (5 cc.) is added to a suspension of 6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-5-phenoxycarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (5.2 g.) in anhydrous dimethylformamide (21 cc.). The reaction mixture is stirred for 15 minutes at a temperature of about 25° C., after which diisopropyl ether (75 cc.) is added. The insoluble product is filtered off, washed with diisopropyl ether (4 × 10 cc.) and then treated with methylene chloride (100 cc.). A slight amount of insoluble matter is filtered off, and the organic solution obtained is then washed by twice successively decanting it with 1N sodium hydroxide solution (25 cc.) and water (25 cc.), dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. After recrystallising the residue obtained from acetonitrile (130 cc.), 6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-5-piperidinocarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]-pyrazine (2.25 g.), melting at 249° C., is obtained.

Aufarbeitung

  1. filtrationThe insoluble product is filtered off
  2. washwashed with diisopropyl ether (4 × 10 cc.)
  3. additiontreated with methylene chloride (100 cc.)
  4. filtrationA slight amount of insoluble matter is filtered off
  5. customthe organic solution obtained
  6. washis then washed
  7. customby twice successively decanting it with 1N sodium hydroxide solution (25 cc.) and water (25 cc.)
  8. dry with materialdried over anhydrous sodium sulphate
  9. customevaporated to dryness under reduced pressure
  10. customAfter recrystallising the residue

Quellen und Nachweise

ORD-Eintrag
ord-a76aab4355a5465e81c4f111b8013de9
Quelldatensatz
uspto-grants-1978_04
Patentnummer
US04086348

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