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 532888Notes

Reaction equation

HRID 532888 reaction equation
[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

Participants

5

Reactant 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

Product 1

HCID 867113419-Bromo-10-fluoro-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-b7ca04d311134c0789de1db61a0833ef
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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