Triethylamine → HCID 178518370, compound

HRID 2236912Notes

Reaction equation

HRID 2236912 reaction equation
[I: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]/OC.[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][N:22]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[C:21](=[O:30])[CH:20]=1.C(N(CC)CC)C>CN(C)C=O>[I: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:17][CH2:18][C:19]1[CH:24]=[CH:23][N:22]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[C:21](=[O:30])[CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68691018(E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneHCID 68694313HCID 68694313, compound

Product 1

HCID 178518370HCID 178518370, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (4E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (97 mg, 0.30 mmol), 4-aminomethyl-1-thiophen-3-yl-1H-pyridin-2-one (61 mg, 0.30 mmol), and triethylamine (77 μL, 0.59 mmol) in N,N-dimethylformamide (2 mL) is stirred overnight at room temperature. The reaction mixture is concentrated under reduced pressure, and the residue is triturated with acetonitrile to provide (4Z)-6-iodo-4-[({[2-oxo-1-(3-thienyl)-1,2-dihydropyridin-4-yl]methyl}amino)methylene]isoquinoline-1,3(2H,4H)-dione as a mauve powder (65 mg, 43%).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue is triturated with acetonitrile

Sources & evidence

ORD record
ord-d72a17e067824c4599c35fd791c767a3
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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