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 532881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 532881
[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-f921885690bc47cfb8b2544858814f07
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853203B2

Notizen zur Reaktion

Wird geladen…