Sodium Iodide → HCID 178480726, compound

HRID 2236940Notes

Reaction equation

HRID 2236940 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH:15]=[C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:26]5[CH:30]=[CH:29][NH:28][CH:27]=5)[CH:24]=4)[C:19](=[O:31])[NH:18][C:17]3=[O:32])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:42][C:43]([NH2:45])=[O:44]>CC(C)=O.CN(C)C=O>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][CH:15]=[C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:26]5[CH:30]=[CH:29][N:28]([CH2:42][C:43]([NH2:45])=[O:44])[CH:27]=5)[CH:24]=4)[C:19](=[O:31])[NH:18][C:17]3=[O:32])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 178480727HCID 178480727, compound

Product 1

HCID 178480726HCID 178480726, compoundYield 17.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-6-(1H-pyrrol-3-yl)-4H-isoquinoline-1,3-dione (42 mg, 0.1 mmol) in acetone (3 mL) and N,N-dimethylformamide (1 mL) is added potassium carbonate (27 mg, 0.2 mmol) and shaken at room temperature for 2 hours. This is followed by addition of sodium iodide (30 mg, 0.2 mmol) and 2-bromoacetamide (17 mg, 0.12 mmol) and further shaking at room temperature overnight. The reaction mixture is then divided into 2 fractions and purified by C18 reverse phase HPLC. The pure fractions were combined and concentrated to yield the title compound (8.4 mg).

Workup

  1. stirringfurther shaking at room temperature overnight
  2. custompurified by C18 reverse phase HPLC
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3e334164d4e74447ac6c5af03cd6bd60
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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