4-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dione → HCID 178518376, compound

HRID 2236885Notes

Reaction equation

HRID 2236885 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([OH:9])[C:6]([O:10][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:5][N:4]=1.CO[CH:20]=[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([I:31])[CH:29]=2)[C:24](=[O:32])[NH:23][C:22]1=[O:33]>CN(C)C=O>[OH:9][C:7]1[C:6]([O:10][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:5][N:4]=[C:3]([CH2:2][NH:1][CH:20]=[C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([I:31])[CH:29]=3)[C:24](=[O:32])[NH:23][C:22]2=[O:33])[CH:8]=1

Participants

4

Reactant 2

HCID 686910194-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dioneHCID 178510260HCID 178510260, compound

Product 1

HCID 178518376HCID 178518376, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-aminomethyl-5-(2-pyrrolidin-1-yl-ethoxy)-pyridin-4-ol (237 mg, 1.0 mmole), 3 mL of N,N-dimethylformamide is stirred, then 4-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dione (329 mg, 1.0 mmole) is added and the reaction mixture stirred for one hour. The reaction mixture is evaporated to dryness, taken up in methanol and purified by HPLC (acetonitrile/water without trifluoroacetic acid); the fractions belonging to the product peak (as determined by MS) were evaporated and still had impurities. This is re-purified by HPLC (acetonitrile water with 0.2% trifluoroacetic acid). The product is isolated by evaporation in-vacuo to give a yellow-orange solid assumed to be the bis trifluoroacetic acid salt, 30 mg, (4%); MS (ES +): m/z 535.1 (M+H).

Workup

  1. stirringthe reaction mixture stirred for one hour
  2. customThe reaction mixture is evaporated to dryness
  3. custompurified by HPLC (acetonitrile/water without trifluoroacetic acid)
  4. customwere evaporated
  5. customThis is re-purified by HPLC (acetonitrile water with 0.2% trifluoroacetic acid)
  6. customThe product is isolated by evaporation in-vacuo
  7. customto give a yellow-orange solid

Sources & evidence

ORD record
ord-acb56cd753a84e5eaa6982a7d696cb11
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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