4-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dione → HCID 178458432, compound

HRID 2236876Notes

Reaction equation

HRID 2236876 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[C:7]([OH:9])[C:6]([O:10][CH2:11][CH2:12][CH3:13])=[CH:5][CH: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[N:8]=[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:4]=[CH:5][C:6]=1[O:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 686910194-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dioneHCID 178458438HCID 178458438, compound

Product 1

HCID 178458432HCID 178458432, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-aminomethyl-3-propoxy-pyridin-2-ol (91 mg, 0.50 mmole), 7 mL of N,N-dimethylformamide is stirred, then 4-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dione (165 mg, 0.50 mmole) is added and the reaction mixture stirred for 4 hours. 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 beige solid, 152 mg, (63%);m.p. 275-81° C. dec; MS (ES +): m/z 478.1 (M+H).

Workup

  1. stirringthe reaction mixture stirred for 4 hours
  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 beige solid, 152 mg, (63%)

Sources & evidence

ORD record
ord-2b325934097642cbb83c7ec382ce9f4d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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