Kojic amine → HCID 178518380, compound

HRID 2236762Notes

Reaction equation

HRID 2236762 reaction equation
[NH2:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([OH:10])[C:7](=[O:9])[CH:8]=1.CO[CH:13]=[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N:24]3[CH:28]=[CH:27][CH:26]=[CH:25]3)[CH:22]=2)[C:17](=[O:29])[NH:16][C:15]1=[O:30]>CN(C)C=O>[OH:10][C:6]1[C:7](=[O:9])[CH:8]=[C:3]([CH2:2][NH:1][CH:13]=[C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([N:24]4[CH:28]=[CH:27][CH:26]=[CH:25]4)[CH:22]=3)[C:17](=[O:29])[NH:16][C:15]2=[O:30])[O:4][CH:5]=1

Participants

4

Reactant 2

HCID 3841Kojic amineHCID 686931254-methoxymethylene-6-pyrrol-1-yl-4H-isoquinoline-1,3-dione

Product 1

HCID 178518380HCID 178518380, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-aminomethyl-5-hydroxy-pyran-4-one (106 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, 157 mg, (55%), mp 310-2° C. dec; MS (ES+): m/z 378.1 (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, 157 mg, (55%), mp 310-2° C. dec

Sources & evidence

ORD record
ord-b05ff891220c4ff0a6c973a4fc872d80
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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