Oxalate → HCID 54319410, compound

HRID 1196720Notes

Reaction equation

HRID 1196720 reaction equation
CN1C(NCCNCCO)=CC(=O)N(C)C1=O.C1(C2OC3C=CC=C(OCCCBr)C=3C(=O)C=2C)C=CC=CC=1.C([O-])(=O)C([O-])=O.C(O)(=O)C(O)=O.[CH3:53][N:54]1[C:59]([NH:60][CH2:61][CH2:62][N:63]([CH2:86][CH2:87][OH:88])[CH2:64][CH2:65][CH2:66][O:67][C:68]2[C:73]3[C:74](=[O:85])[C:75]([CH3:84])=[C:76]([C:78]4[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=4)[O:77][C:72]=3[CH:71]=[CH:70][CH:69]=2)=[CH:58][C:57](=[O:89])[N:56]([CH3:90])[C:55]1=[O:91]>CN(C)C=O.C(N(CC)CC)C>[CH3:53][N:54]1[C:59]([NH:60][CH2:61][CH2:62][N:63]([CH2:86][CH2:87][OH:88])[CH2:64][CH2:65][CH2:66][O:67][C:68]2[C:73]3[C:74](=[O:85])[C:75]([CH3:84])=[C:76]([C:78]4[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=4)[O:77][C:72]=3[CH:71]=[CH:70][CH:69]=2)=[CH:58][C:57](=[O:89])[N:56]([CH3:90])[C:55]1=[O:91]

Participants

7

Reactant 4

HCID 71081OxalateHCID 19898742HCID 19898742, compound2×HCID 19898743HCID 19898743, compound2×HCID 67794760HCID 67794760, compound

Product 1

HCID 54319410HCID 54319410, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

In 5 ml of N,N-dimethylformamide, reaction was carried out at 90° C. for 1 hour among 0.68 g of 1,3-dimethyl-6-[2-(2-hydroxyethylamino)ethylamino]-2,4-(1H,3H)-pyrimidinedione (Compound 15), 0.96 g of 3-(2-phenyl-3-methyl-4-oxo-4H-1-benzopyran-5-yl)oxypropyl bromide (Compound 16) and 1 ml of triethylamine. The resultant reaction solution was concentrated under reduced pressure, and the residue was dissolved in chloroform and then washed with water. The thus water-washed chloroform layer was dried over anhydrous sodium sulfate, and then purified through a silica gel column chromatograph (chloroform:methanol=98:2 to 96:4 in volume ratio) in odrer to obtain 0.75 g (yield 55%) of 1,3-dimethyl-6-(2-[N-hydroxyethyl-N-[3-(2-phenyl-3-methyl-4-oxo-4H-1-benzopyran-5-yl)oxypropyl]amino]ethyl-amino)-2,4(1H,3H)-pyrimidinedione (the non-oxalate of Compound 17).

Workup

  1. customThe resultant reaction solution
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washwashed with water
  5. washThe thus water-washed chloroform layer
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. custompurified through a silica gel column chromatograph (chloroform:methanol=98:2 to 96:4 in volume ratio) in odrer

Sources & evidence

ORD record
ord-69811d6cb42e4ffeb56690794899799e
Source dataset
uspto-grants-1992_05
Patent number
US05114941

Reaction notes

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