Triethylamine → 4-[[(5-amino-4-oxo-1H-pyridin-2-yl)methylamino]methylidene]-6-iodoisoquinoline-1,3-dione

HRID 2236823Notes

Reaction equation

HRID 2236823 reaction equation
[NH2:1][C:2]1[C:3]([OH:10])=[CH:4][C:5]([CH2:8][NH2:9])=[N:6][CH:7]=1.C(N(CC)CC)C.CO[CH:20]=[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([I:31])[CH:29]=2)[C:24](=[O:32])[NH:23][C:22]1=[O:33]>CN(C)C=O>[NH2:1][C:2]1[C:3]([OH:10])=[CH:4][C:5]([CH2:8][NH:9][CH:20]=[C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([I:31])[CH:29]=3)[C:24](=[O:32])[NH:23][C:22]2=[O:33])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 686910194-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dioneHCID 1785102595-Amino-2-aminomethyl-pyridin-4-ol

Product 1

HCID 1785080254-[[(5-amino-4-oxo-1H-pyridin-2-yl)methylamino]methylidene]-6-iodoisoquinoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-amino-2-aminomethyl-pyridin-4-ol (60 mg, 0.19 mmole as the dihydrobromide), 3 mL of N,N-dimethylformamide and triethylamine (101 uL, 0.72 mmole) were stirred for 15 mins, 4-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dione (63 mg, 0.19 mmole) is added and the reaction mixture stirred for one hour. The reaction mixture is evaporated to dryness, taken up in dimethylsulfoxide and purified by HPLC (acetonitrile-water with 0.2% trifluoroacetic acid). The product is isolated by evaporation in-vacuo to give a brown solid, 5.5 mg, (5%); MS (ES+): m/z 437.0 (M+H).

Workup

  1. stirringthe reaction mixture stirred for one hour
  2. customThe reaction mixture is evaporated to dryness
  3. custompurified by HPLC (acetonitrile-water with 0.2% trifluoroacetic acid)
  4. customThe product is isolated by evaporation in-vacuo
  5. customto give a brown solid, 5.5 mg, (5%)

Sources & evidence

ORD record
ord-1eb632d4d7ce43f49177dc646dd70360
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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