Hydrochloric Acid → 9-Iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 532874Notes

Reaction equation

HRID 532874 reaction equation
[Cl-].[C:2]([CH2:5][CH:6]1[C:15]2[C:10](=[C:11]([I:16])[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][N:7]1[C:17](=[O:20])[CH2:18][NH3+:19])(O)=[O:3].C(OC(NCC(N1CCC2C(=CC=CC=2I)C1CC([O-])=O)=O)=O)(C)(C)C.[Na+].Cl>O1CCOCC1>[I:16][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[CH2:9][CH2:8][N:7]1[C:17](=[O:20])[CH2:18][NH:19][C:2](=[O:3])[CH:5]=[C:6]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86711322Sodium 2-(2-(2-((tert-butoxycarbonyl)amino)acetyl)-5-iodo-1,2,3,4-tetrahydroisoquinolin-1-yl)acetateHCID 867113252-(1-(carboxymethyl)-5-iodo-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanaminium chloride

Product 1

HCID 867113799-Iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(1-(carboxymethyl)-5-iodo-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanaminium chloride. A suspension of sodium 2-(2-(2-((tert-butoxycarbonyl)amino)acetyl)-5-iodo-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate (49.8 g, 100 mmol) in dry dioxane (1 L) was treated with an aqueous solution of HCl (4M, 280 ml, 1.12 mol) and the mixture was stirred at RT for 18 h. The reaction mixture was then concentrated in vacuo to give the title compound (46.1 g) as a beige powder that was used as it is in the next step. UPLC-MS: MS 375.1 (M+H+); UPLC rt 0.60 min.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-51cb428dae54415a92b4352b7dfe8c1e
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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