2-(5-Bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-yl)acetic acid → 9-Bromo-10-fluoro-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 532888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 532888
[NH2:1][CH2:2][C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:16])[C:11]=2[Br:15])[CH:6]1[CH2:17][C:18]([OH:20])=O)=[O:4].BrC1C(F)=CC=C2C=1CCN(C(=O)CNC(OC(C)(C)C)=O)C2CC(O)=O>O1CCOCC1.Cl>[Br:15][C:11]1[C:10]([F:16])=[CH:9][CH:8]=[C:7]2[C:12]=1[CH2:13][CH2:14][N:5]1[C:3](=[O:4])[CH2:2][NH:1][C:18](=[O:20])[CH:17]=[C:6]12

Komponenten

5

Edukt 2

HCID 867113382-(5-Bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-yl)acetic acidHCID 867113392-(2-(2-aminoacetyl)-5-bromo-6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-yl)acetic Acid

Produkt 1

HCID 867113419-Bromo-10-fluoro-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-(2-(2-aminoacetyl)-5-bromo-6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-yl)acetic Acid (HCl Salt). To a stirred solution of 2-(5-bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-yl)acetic acid (58.45 g, 131 mmol) in dioxane (600 mL), 4N HCl in dioxane (328 mL, 1313 mmol) was added and the reaction mixture was stirred at RT for 24 h. The solvent was evaporated under reduced pressure and the HCl salt was dried under high vacuo overnight to yield the title compound as yellow foam (54.6 g). UPLC-MS: MS 345.2/347.2 (M+H+); UPLC rt 0.56 min.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. dry with materialthe HCl salt was dried under high vacuo overnight

Quellen und Nachweise

ORD-Eintrag
ord-b7ca04d311134c0789de1db61a0833ef
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853203B2

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