Glycine ethyl ester, hydrochloride → 9-methoxy-2-(3-methoxyphenyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

HRID 532907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 532907
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7]/[C:8]/2=[CH:13]\[C:14](=[N:23]/[CH2:24][C:25](OCC)=[O:26])\[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1.Cl.C(OC(=O)CN)C>CCO.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]1[C:25](=[O:26])[CH2:24][N:23]=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[CH:13]=[C:8]12

Komponenten

5

Edukt 2

HCID 2723640Glycine ethyl ester, hydrochlorideHCID 178472709HCID 178472709, Verbindung

Produkt 1

HCID 733348529-methoxy-2-(3-methoxyphenyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

ethyl 2-((E)-((Z)-2-(5-methoxy-3,4-dihydroisoquinolin-1(2H)-ylidene)-1-(3-methoxyphenyl)ethylidene)amino)acetate. 1-2. A mixture of 1-1 (5.8 g, 18.81 mmol) and glycine ethyl ester hydrochloride (13.1 g, 94 mmol) in EtOH (200 mL) was heated to 100° C. and stirred for 2 h. The reaction was then cooled to RT and the mixture was concentrated in vacuo. The residue obtained was taken up in DCM and washed with a 1M aq. solution of NaOH. The org. layer was then dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (7.0 g) as a brown oil that was used as it is in the next step. UPLC-MS: MS 395.3 (M+H+); UPLC rt 0.80 min.

Aufarbeitung

  1. temperatureThe reaction was then cooled to RT
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue obtained
  4. washwashed with a 1M aq. solution of NaOH
  5. dry with materiallayer was then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5577c5e4fe8f45a4a362b81cae9643f6
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853203B2

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