2-(5-bromo-1-(carboxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanaminium chloride → 9-Bromo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 926254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926254
[Cl-].[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]([C:17](=[O:20])[CH2:18][NH3+:19])[CH:8]2[CH2:13][C:14](O)=[O:15].BrC1C=CC=C2C=1CCN(C(=O)CNC(OC(C)(C)C)=O)C2CC(O)=O>O1CCOCC1.Cl>[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]1[C:17](=[O:20])[CH2:18][NH:19][C:14](=[O:15])[CH:13]=[C:8]12

Komponenten

5

Edukt 2

HCID 867113302-(5-bromo-1-(carboxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanaminium chlorideHCID 867113322-(5-Bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)acetic acid

Produkt 1

HCID 867113289-Bromo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

2-(5-bromo-1-(carboxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanaminium chloride. To a stirred solution of 2-(5-bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)acetic acid (110 g, 257 mmol) in dioxane (1290 mL), 4N HCl in dioxane (644 mL, 2574 mmol) was added and the reaction mixture was stirred at RT for 24 h. The white precipitate was filtered off and the white solid was washed with a small amount of diethyl ether (2×). The HCl salt was dried under high vacuo overnight to yield the title compound as white solid (88 g). UPLC-MS: MS 327.1/329.1 (M+H+); UPLC rt 0.56 min.

Aufarbeitung

  1. filtrationThe white precipitate was filtered off
  2. washthe white solid was washed with a small amount of diethyl ether (2×)
  3. dry with materialThe HCl salt was dried under high vacuo overnight

Quellen und Nachweise

ORD-Eintrag
ord-9c946f762c124ac3bbbf926c9d074485
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284331B2

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