Triethylamine → HCID 178448496, compound

HRID 2236894Notes

Reaction equation

HRID 2236894 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.FC(F)(F)C(O)=O.[NH2:24][CH2:25][C:26]1[CH:31]=[CH:30][N:29]([CH2:32][CH2:33][CH2:34][CH3:35])[C:28](=[O:36])[CH:27]=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:24][CH2:25][C:26]1[CH:31]=[CH:30][N:29]([CH2:32][CH2:33][CH2:34][CH3:35])[C:28](=[O:36])[CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68691018(E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneHCID 68693777HCID 68693777, compound

Product 1

HCID 178448496HCID 178448496, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (4E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (170 mg, 0.51 mmol) and 4-aminomethyl-1-butyl-1H-pyridin-2-one trifluoroacetate (150 mg, 0.51 mol) is stirred in dimethylformamide (2.7 mL) at room temperature in the presence of triethylamine (0.33 mL) for 18 hours. The reaction mixture is concentrated under reduced pressure. The residue is purified via semi-preparative HPLC (Prodigy ODS3 column, 5% acetonitrile/95% water/0.01% trifluoroacetic acid to 100% acetonitrile at 10 mL/min) to give (4Z)-6-iodo-4-({[(1-butyl-2-oxo-1,2-dihydropyridin-4-yl)methyl]amino}methylene)isoquinoline-1,3(2H,4H)-dione as an peach colored solid (25 mg, 10% due to substantial loss of material during HPLC malfunction).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customThe residue is purified via semi-preparative HPLC (Prodigy ODS3 column, 5% acetonitrile/95% water/0.01% trifluoroacetic acid to 100% acetonitrile at 10 mL/min)

Sources & evidence

ORD record
ord-5f0e5ec865b74a9bbe007928a3a7b8b7
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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