Triethylamine → HCID 178440612, compound

HRID 2236898Notes

Reaction equation

HRID 2236898 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:10][C:9](=[O:16])/[C:8]/2=[CH:17]/OC)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][N:26]([C:29]2[CH:33]=[CH:32][O:31][CH:30]=2)[C:25](=[O:34])[CH:24]=1.C(N(CC)CC)C>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:10][C:9](=[O:16])/[C:8]/2=[CH:17]\[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][N:26]([C:29]2[CH:33]=[CH:32][O:31][CH:30]=2)[C:25](=[O:34])[CH:24]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 42625173(4E)-6-t-butyl-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneHCID 426257504-aminomethyl-1-furan-3-yl-1H-pyridin-2-one hydrochloride

Product 1

HCID 178440612HCID 178440612, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (4E)-6-tert-butyl-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (50 mg, 0.19 mmol), 4-aminomethyl-1-furan-3-yl-1H-pyridin-2-one hydrochloride (43 mg, 0.19 mmol), and triethylamine (150 μL, 1.1 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 chloroform to provide (4Z)-6-tert-butyl-4-[({[1-(3-furyl)-2-oxo-1,2-dihydropyridin-4-yl]methyl}amino)methylene]isoquinoline-1,3(2H,4H)-dione as a white solid (34 mg, 43%).

Workup

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

Sources & evidence

ORD record
ord-18c373b4d6044471a7910f67fe442242
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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