Dimethyl Sulfoxide → HCID 135554981, compound

HRID 1534964Notes

Reaction equation

HRID 1534964 reaction equation
[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13](OC3C=CC([N+]([O-])=O)=CC=3)=O)[CH:5]=[N:4][C:3]1=2.[C:25]1([N:31]2[C:35]3([CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[C:34](=[O:41])[NH:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CS(C)=[O:44]>>[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][C:12](=[O:44])[CH2:13][N:38]3[CH2:37][CH2:36][C:35]4([N:31]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)[CH2:32][NH:33][C:34]4=[O:41])[CH2:40][CH2:39]3)[CH:5]=[N:4][C:3]1=2

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 1359739573-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester

Product 1

HCID 135554981HCID 135554981, compoundYield 90%

Procedure

0.300 g (0.9111 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-propanoic acid, 4-nitrophenyl ester (AIT-0081) and 0.212 g (0.9165 mmol) of 1-phenyl-1,3,8-triazaspiro[4.5]decane-4-one were placed into a 10 ml round bottom flask equipped with a magnetic stirring bar. 2 ml of dimethylsulfoxide (dried over barium oxide) was added and the solution was stirred in a closed flask at room temperature for 20 hours. The reaction was allowed to proceed overnight to ensure completion. The solvent was removed with vacuum using gentle heat (approximately 45 deg.). 10 ml ethyl acetate was added to the stirring residue (oil) and a copious white precipitate formed immediately. The solution was stirred for 30 minutes to ensure homogeneity. Upon filtration, washing with ethyl acetate, and drying, 345 mg of a free flowing white solid, 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-(1-phenyl-4-oxo-1,3,8-triazaspiro[4.5]dec-8-yl)propanone (AIT-0098) was obtained. Yield: 90%.

Workup

  1. customequipped with a magnetic stirring bar
  2. waitto proceed overnight
  3. customThe solvent was removed with vacuum
  4. temperatureusing gentle heat (approximately 45 deg.)
  5. addition10 ml ethyl acetate was added to the stirring residue (oil)
  6. customa copious white precipitate formed immediately
  7. stirringThe solution was stirred for 30 minutes
  8. filtrationUpon filtration
  9. washwashing with ethyl acetate
  10. customdrying
  11. customwas obtained

Sources & evidence

ORD record
ord-47e9975f856f43caac2950406236f1c0
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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