4-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dione → 6-iodo-4-[[(4-oxo-5-propoxy-1H-pyridin-2-yl)methylamino]methylidene]isoquinoline-1,3-dione

HRID 2236795Notes

Reaction equation

HRID 2236795 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([OH:9])[C:6]([O:10][CH2:11][CH2:12][CH3:13])=[CH:5][N:4]=1.CO[CH:16]=[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([I:27])[CH:25]=2)[C:20](=[O:28])[NH:19][C:18]1=[O:29]>CN(C)C=O>[OH:9][C:7]1[C:6]([O:10][CH2:11][CH2:12][CH3:13])=[CH:5][N:4]=[C:3]([CH2:2][NH:1][CH:16]=[C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([I:27])[CH:25]=3)[C:20](=[O:28])[NH:19][C:18]2=[O:29])[CH:8]=1

Participants

4

Reactant 2

HCID 686910194-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dioneHCID 178458783HCID 178458783, compound

Product 1

HCID 1784587876-iodo-4-[[(4-oxo-5-propoxy-1H-pyridin-2-yl)methylamino]methylidene]isoquinoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-aminomethyl-5-propoxy-pyridin-4-ol (137 mg, 0.75 mmole) in 10 mL of N,N-dimethylformamide is stirred, then 4-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dione (247 mg, 0.75 mmole) is added and the reaction mixture stirred for one hour. The reaction mixture is evaporated to dryness, triturated with 5% methanol in chlororform, filtered washed with fresh 5% methanol in chloroform, washed with acetonitrile and dried to give a pink solid, 313 mg, (87%); MS (ES+): m/z 479.9 (M+H).

Workup

  1. stirringthe reaction mixture stirred for one hour
  2. customThe reaction mixture is evaporated to dryness
  3. customtriturated with 5% methanol in chlororform
  4. filtrationfiltered
  5. washwashed with fresh 5% methanol in chloroform
  6. washwashed with acetonitrile
  7. customdried
  8. customto give a pink solid, 313 mg, (87%)

Sources & evidence

ORD record
ord-6c80eea9a0e0400dab31d373c2e09f4f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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