6-Furan-2-yl-4-methoxymethylene-4H-isoquinoline-1,3-dione → HCID 178458785, compound

HRID 2236870Notes

Reaction equation

HRID 2236870 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]([C:27]3[O:28][CH:29]=[CH:30][CH:31]=3)[CH:25]=2)[C:20](=[O:32])[NH:19][C:18]1=[O:33]>CN(C)C=O>[O:28]1[CH:29]=[CH:30][CH:31]=[C:27]1[C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:32])[NH:19][C:18](=[O:33])[C:17]2=[CH:16][NH: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

Participants

4

Reactant 2

HCID 686963676-Furan-2-yl-4-methoxymethylene-4H-isoquinoline-1,3-dioneHCID 178458783HCID 178458783, compound

Product 1

HCID 178458785HCID 178458785, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-aminomethyl-5-propoxy-pyridin-4-ol (73 mg, 0.40 mmole), 5 mL of N,N-dimethylformamide is stirred, then 4-methoxymethylene-6-(furan-2-yl)-4H-isoquinoline-1,3-dione (108 mg, 0.40 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 pale yellow solid, 139 mg, (83%); m.p. 288-90° C. dec; MS (ES+): m/z 420.2 (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 pale yellow solid, 139 mg, (83%)

Sources & evidence

ORD record
ord-f5bec7bfcdb84dc18da53d4d4886da4d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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