Water → HCID 178458427, compound

HRID 2236654Notes

Reaction equation

HRID 2236654 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:10][CH2:11][CH2:12][CH3:13])=[C:7]([OH:9])[CH:8]=1.C(N(CC)CC)C.[I:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[C:28](=[O:32])[NH:27][C:26](=[O:33])/[C:25]/2=[CH:34]/OC.O>CN(C)C=O>[OH:9][C:7]1[CH:8]=[C:3]([CH:4]=[CH:5][C:6]=1[O:10][CH2:11][CH2:12][CH3:13])[CH2:2][NH:1]/[CH:34]=[C:25]1\[C:26](=[O:33])[NH:27][C:28](=[O:32])[C:29]2[C:24]\1=[CH:23][C:22]([I:21])=[CH:31][CH:30]=2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 219043645-(Aminomethyl)-2-propoxyphenolHCID 68691018(E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178458427HCID 178458427, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An amount of 5-(aminomethyl)-2-propoxyphenol (60 mg, 0.33 mmol) is dissolved in N,N-dimethylformamide (2 mL). 0.137 m/(1.0 mmol) of triethylamine is added followed by 100 mg (0.30 mmol) of (4E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione. After the mixture is stirred at room temperature for 30 min, water (5 mL) is added and the reaction mixture is stirred for 60 min. The precipitate is filtered and washed several times with anhydrous ether. The crude solid is then purified by high performance liquid chromatography to give 54 mg of a white solid. MS (ESI) m/z 480.3 (M+1).

Workup

  1. stirringthe reaction mixture is stirred for 60 min
  2. filtrationThe precipitate is filtered
  3. washwashed several times with anhydrous ether
  4. customThe crude solid is then purified by high performance liquid chromatography

Sources & evidence

ORD record
ord-e121b175296540ad99c95a778e3648fd
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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