4-(5-Methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)aniline → 6-iodo-4-[[4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)anilino]methylidene]isoquinoline-1,3-dione

HRID 2236680Notes

Reaction equation

HRID 2236680 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]2[CH2:8][CH:3]1[CH2:4][N:5]2[C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1.[I:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[NH:22][C:21](=[O:28])[C:20]2=[CH:29]OC>CN(C)C=O>[I:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[NH:22][C:21](=[O:28])[C:20]2=[CH:29][NH:15][C:12]1[CH:13]=[CH:14][C:9]([N:5]2[CH2:4][CH:3]3[CH2:8][CH:6]2[CH2:7][N:2]3[CH3:1])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 594103234-(5-Methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)anilineHCID 686910194-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dione

Product 1

HCID 1784798916-iodo-4-[[4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)anilino]methylidene]isoquinoline-1,3-dioneYield 39.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(5-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamine (0.1 g, 0.49 mmol), 6-Iodo-4-methoxymethylene-4H-isoquinoline-1,3-dione (0.2 g, 0.6 mmol), and N,N-dimethylformamide (0.2 mL) is heated at 90° C. overnight. After the solvent is removed, the residue is treated with ethyl ether and filtered to give crude product as light brown solid. It is purified by HPLC to yield 97 mg (39% yield) of 6-iodo-4-{[4-(5-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamino]-methylene}-4H-isoquinoline-1,3-dione as bright orange solid. mp 210-211° C.

Workup

  1. customAfter the solvent is removed
  2. additionthe residue is treated with ethyl ether
  3. filtrationfiltered
  4. customto give crude product as light brown solid
  5. customIt is purified by HPLC

Sources & evidence

ORD record
ord-de85438fa87247b6a6082de3742459cd
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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