Acetone → 4-[3-(6-Oxo-1,6-dihydropurin-9-yl)propionylamino]benzoic acid ethyl ester

HRID 1534953Notes

Reaction equation

HRID 1534953 reaction equation
[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([O:15]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH:5]=[N:4][C:3]1=2.[CH2:25]([O:27][C:28](=[O:36])[C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=1)[CH3:26].CC(C)=O>CS(C)=O>[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([NH:35][C:32]3[CH:31]=[CH:30][C:29]([C:28]([O:27][CH2:25][CH3:26])=[O:36])=[CH:34][CH:33]=3)=[O:15])[CH:5]=[N:4][C:3]1=2

Participants

5

Reactant 3

HCID 180AcetoneHCID 2337BenzocaineHCID 1359739573-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester

Product 1

HCID 1354951274-[3-(6-Oxo-1,6-dihydropurin-9-yl)propionylamino]benzoic acid ethyl esterYield 30%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

165 mg (0.50 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester (AIT-0081) and 84 mg (0.50 mmol) of 4-aminobenzoic acid ethyl ester were heated together in 1.5 ml of dimethylsulfoxide at 35°-40° C. for 72 hours. A white precipitate was observed at the bottom of the flask. 10 ml acetone was added and the solid was collected by Buchner vacuum filtration. The solid was washed twice with acetone and was allowed to dry. This yielded 53 mg of 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]benzoic acid, ethyl ester (AIT-0079) as a white solid. m.p. 265°-269° C. Yield: 30%.

Workup

  1. filtrationthe solid was collected by Buchner vacuum filtration
  2. washThe solid was washed twice with acetone
  3. customto dry

Sources & evidence

ORD record
ord-0ff2c88dd776414380cf444d992e1292
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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