2-Aminomethyl-5-methoxy-pyran-4-one → HCID 178493895, compound

HRID 2236766Notes

Reaction equation

HRID 2236766 reaction equation
[NH2:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([O:10][CH3:11])[C:7](=[O:9])[CH:8]=1.CO[CH:14]=[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([Br:25])[CH:23]=2)[C:18](=[O:26])[NH:17][C:16]1=[O:27]>CN(C)C=O>[Br:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:26])[NH:17][C:16](=[O:27])[C:15]2=[CH:14][NH:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([O:10][CH3:11])[C:7](=[O:9])[CH:8]=1

Participants

4

Reactant 2

HCID 50798292-Aminomethyl-5-methoxy-pyran-4-oneHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

Product 1

HCID 178493895HCID 178493895, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-aminomethyl-5-methoxy-pyran-4-one (116 mg, 0.75 mmole), 4 mL of N,N-dimethylformamide and 4-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione (212 mg, 0.75 mmole) is stirred for one hour at ambient temperature. The reaction mixture is evaporated to dryness, dissolved in 7.5% methanol in chloroform passed through Florisil eluting with 7.5% methanol in chloroform. The eluate is evaporated, treated with acetonitrile, the resulting solid filtered and dried to give a light pink solid, 152 mg, (50%), mp 259-61° C. dec; MS (ES−): m/z 403 (M−H).

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. dissolutiondissolved in 7.5% methanol in chloroform
  3. customThe eluate is evaporated
  4. additiontreated with acetonitrile
  5. filtrationthe resulting solid filtered
  6. customdried
  7. customto give a light pink solid, 152 mg, (50%), mp 259-61° C. dec

Sources & evidence

ORD record
ord-9c7df208d5b24fb0a7f2486ebd9b2d2e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…