Dimethyl Sulfoxide → 4-[[2-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1oxopropyl]amino]ethyl]amino]-2-hydroxy-4-oxo-N,N,N-trimethyl-1-butanaminium chloride

HRID 1534959Notes

Reaction equation

HRID 1534959 reaction equation
[Cl-:1].[NH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:15])[CH2:7][CH:8]([OH:14])[CH2:9][N+:10]([CH3:13])([CH3:12])[CH3:11].CS(C)=O.[O:20]=[C:21]1[NH:29][CH:28]=[N:27][C:26]2[N:25]([CH2:30][CH2:31][C:32](OC3C=CC([N+]([O-])=O)=CC=3)=[O:33])[CH:24]=[N:23][C:22]1=2.CO>CC(C)=O>[Cl-:1].[O:20]=[C:21]1[NH:29][CH:28]=[N:27][C:26]2[N:25]([CH2:30][CH2:31][C:32]([NH:2][CH2:3][CH2:4][NH:5][C:6](=[O:15])[CH2:7][CH:8]([OH:14])[CH2:9][N+:10]([CH3:13])([CH3:12])[CH3:11])=[O:33])[CH:24]=[N:23][C:22]1=2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 887MethanolHCID 199086104-[(2-aminoethyl)amino]-2-hydroxy-4-oxo-N,N,N-trimethyl-1-butanaminium chlorideHCID 1359739573-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester

Product 1

HCID 1364033604-[[2-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1oxopropyl]amino]ethyl]amino]-2-hydroxy-4-oxo-N,N,N-trimethyl-1-butanaminium chlorideYield 33%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

248 mg (1.0344 mmol) of 4-[(2-aminoethyl)amino]-2-hydroxy-4-oxo-N,N,N-trimethyl-1-butanaminium chloride was placed into a 10 ml round bottom flask with magnetic stirring bar. Then 2 ml of dimethylsulfoxide was added and the solution was gently heated to help dissolve the amine. 340 mg (1.034 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester (AIT-0081) was added to the stirring solution. The solution was stirred for a period of one hour and 3 ml of methanol was added. Then 3 ml of acetone was added and the solution was filtered. The solid was washed several times with acetone and allowed to dry. This yielded 105 mg of 4-[[2-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]ethyl]amino]-2-hydroxy-4-oxo-N,N,N-trimethyl-1-butanaminium chloride (AIT-0090) as a white solid. m.p. approximately 260-265 (dec) Yield: 33%.

Workup

  1. temperaturethe solution was gently heated
  2. filtrationthe solution was filtered
  3. washThe solid was washed several times with acetone
  4. customto dry

Sources & evidence

ORD record
ord-bc0906d2659947b7bfb8195addec47ba
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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