Potassium Carbonate → HCID 178458731, compound

HRID 2236666Notes

Reaction equation

HRID 2236666 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][CH2:16][C:17]1[CH:22]=[C:21]([OH:23])[CH:20]=[C:19]([OH:24])[CH:18]=1.I[CH2:26][CH2:27][CH3:28].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14][NH:15][CH2:16][C:17]1[CH:18]=[C:19]([O:24][CH2:26][CH2:27][CH3:28])[CH:20]=[C:21]([OH:23])[CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 178518282HCID 178518282, compound

Product 1

HCID 178458731HCID 178458731, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

(4Z)-6-bromo-4-{[(3,5-dihydroxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione (50 mg, 0.128 mmol) is dissolved in 1 mL N,N-dimethylformamide (DMF) (1 mL). To the resulting solution is added 1-iodo-propane (25 μL, 0.256 mmol) and K2CO3 (53 mg, 0.384 mmol). The reaction mixture is heated at 100° C. for 2 hours. The solid is filtered and purified by HPLC eluting with 20% CH3CN/H2O to 100% CH3CN over 30 minutes to give 19 mg (34%) of the title compound as a tan powder. MS (ESI) m/z 431.1(M+H)+

Workup

  1. filtrationThe solid is filtered
  2. custompurified by HPLC
  3. washeluting with 20% CH3CN/H2O to 100% CH3CN over 30 minutes

Sources & evidence

ORD record
ord-a50d5450e9ba4685ae2f63032cd66bf6
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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