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 926261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926261
[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-c446ec5aa9e0491b9bd5c057e2f75e02
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284331B2

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