2-Aminomethyl-5-methoxy-pyran-4-one → HCID 178493896, compound

HRID 2236767Notes

Reaction equation

HRID 2236767 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]([N:25]3[CH:29]=[CH:28][CH:27]=[CH:26]3)[CH:23]=2)[C:18](=[O:30])[NH:17][C:16]1=[O:31]>CN(C)C=O>[CH3:11][O:10][C:6]1[C:7](=[O:9])[CH:8]=[C:3]([CH2:2][NH:1][CH:14]=[C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([N:25]4[CH:29]=[CH:28][CH:27]=[CH:26]4)[CH:23]=3)[C:18](=[O:30])[NH:17][C:16]2=[O:31])[O:4][CH:5]=1

Participants

4

Reactant 2

HCID 50798292-Aminomethyl-5-methoxy-pyran-4-oneHCID 686931254-methoxymethylene-6-pyrrol-1-yl-4H-isoquinoline-1,3-dione

Product 1

HCID 178493896HCID 178493896, 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-pyrrol-1-yl-4H-isoquinoline-1,3-dione (201 mg, 0.80 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 beige solid, 106 mg, (36%), mp 251-4° C. dec; MS (ES−): m/z 390.1 (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 beige solid, 106 mg, (36%), mp 251-4° C. dec

Sources & evidence

ORD record
ord-0519a5b404a64756b514b3c33e9d8de5
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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