Triphenylphosphine → 2-Chloro-5,11-dihydro-11-ethyl-4-methyl-8-{2-(5-quinolinyloxy)ethyl}-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 2229336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229336
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[CH:15]=[C:16]([CH3:35])[C:17]2[NH:18][C:19](=[O:34])[C:20]3[CH:30]=[C:29]([CH2:31][CH2:32][OH:33])[CH:28]=[N:27][C:21]=3[N:22]([CH2:25][CH3:26])[C:23]=2[N:24]=1.O[C:37]1[CH:46]=[CH:45][CH:44]=[C:43]2[C:38]=1[CH:39]=[CH:40][CH:41]=[N:42]2.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.CCOC(C)=O>[Cl:13][C:14]1[CH:15]=[C:16]([CH3:35])[C:17]2[NH:18][C:19](=[O:34])[C:20]3[CH:30]=[C:29]([CH2:31][CH2:32][O:33][C:37]4[CH:46]=[CH:45][CH:44]=[C:43]5[C:38]=4[CH:39]=[CH:40][CH:41]=[N:42]5)[CH:28]=[N:27][C:21]=3[N:22]([CH2:25][CH3:26])[C:23]=2[N:24]=1

Komponenten

7

Edukt 4

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 184666082-chloro-5,11-dihydro-11-ethyl-8-(2-hydroxyethyl)4methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneHCID 135441757Quinolin-5-ol

Produkt 1

HCID 30106672-Chloro-5,11-dihydro-11-ethyl-4-methyl-8-{2-(5-quinolinyloxy)ethyl}-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Diethyl azodicarboxylate (DEAD) (77 μL, 0.49 mmol) was added drop wise to a solution of 2-chloro-5,11-dihydro-11-ethyl-8-(2-hydroxyethyl)4methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (125 mg, 0.38 mmol), 5-hydroxyquinoline (70.9 mg, 0.49 mmol) and Ph3P (128 mg, 0.49 mmol) in THF (2.5 mL) at room temperature. After 1.5 h, additional amounts of DEAD (35 μL, 0.22 mmol) and PPh3 (59 mg, 0.22 mmol) were added to the mixture. The mixture was stirred at room temperature for 1 h then was diluted in EtOAc (50 mL) and the solution was successively washed with aqueous 1 N NaOH (4×10 mL) and brine (15 mL) then was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2:acetone, 85:15). The resulting solid was triturated with Et2O to give the title compound (38 mg, 22% yield) as a white solid: MS (ESI) m/z 460/462 (MH)+.

Aufarbeitung

  1. washthe solution was successively washed with aqueous 1 N NaOH (4×10 mL) and brine (15 mL)
  2. dry with materialthen was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (CH2Cl2:acetone, 85:15)
  6. customThe resulting solid was triturated with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-bdbde76c97be4ebdb50675cf1a335b0c
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420359B1

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