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 926254Notes

Reaction equation

HRID 926254 reaction equation
[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

Participants

5

Reactant 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

Product 1

HCID 867113289-Bromo-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-(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.

Workup

  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

Sources & evidence

ORD record
ord-9c946f762c124ac3bbbf926c9d074485
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

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