Triethylamine → HCID 86619587, compound

HRID 2236728Notes

Reaction equation

HRID 2236728 reaction equation
Cl.[F:2][CH:3]([F:14])[O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][C:6]=1[OH:13].C(N(CC)CC)C.[I:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29](=O)[NH:28][C:27](=O)/[C:26]/2=[CH:35]/OC>CN(C)C=O>[I:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[CH:29]=[N:28][CH2:27]/[C:26]/2=[CH:35]\[NH:10][CH2:9][C:8]1[CH:11]=[CH:12][C:5]([O:4][CH:3]([F:14])[F:2])=[C:6]([OH:13])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68691018(E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneHCID 68694285HCID 68694285, compound

Product 1

HCID 86619587HCID 86619587, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An amount of 4-difluoromethoxy-3-hydroxy benzylamine hydrochloride (113 mg, 0.50 mmol), is dissolved in N,N-dimethylformamide (5 mL), triethylamine (50 μL 0.75 mmol) is added followed by (4E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (165 mg, 0.50 mmol). After the mixture is stirred at room temperature for 30 min, the solvent is removed in-vacuo and the residue dissolved in 7.5% methanol in chloroform and passed thru a short pad of Florisil eluting with 7.5% methanol in chloroform, the eluate is evaporated and the solid triturated with ether, filtered and washed several times with anhydrous ether to give 193 mg of (4Z)-6-Iodo-4-{[(4-difluoromethoxy-3-hydroxybenzyl)amino)methylene}isoquinoline-1,3(2H,4-dione as a beige solid (79% yield); mp 254-5° C., MS data ES(−) 485.0 m/e.

Workup

  1. customthe solvent is removed in-vacuo
  2. dissolutionthe residue dissolved in 7.5% methanol in chloroform
  3. customthe eluate is evaporated
  4. customthe solid triturated with ether
  5. filtrationfiltered
  6. washwashed several times with anhydrous ether

Sources & evidence

ORD record
ord-770ba2c7be9845acabbabf748f9301f5
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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