Acetonitrile → HCID 136403356, compound

HRID 1534939Notes

Reaction equation

HRID 1534939 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH2:7])(=[O:3])[CH3:2].[O:8]=[C:9]1[NH:17][CH:16]=[N:15][C:14]2[N:13]([CH2:18][CH2:19][C:20]([O:22]CC)=O)[CH:12]=[N:11][C:10]1=2.C(#N)C>CO>[O:8]=[C:9]1[NH:17][CH:16]=[N:15][C:14]2[N:13]([CH2:18][CH2:19][C:20]([NH:7][CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])=[O:22])[CH:12]=[N:11][C:10]1=2

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 66082N-(2-aminoethyl)acetamideHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 136403356HCID 136403356, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

0.516 g (5.05 mmol) of N-acetylethylenediamine was placed into a 10 ml round bottom flask. The flask was heated to 120° C. and 0.250 g (1.06 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) was added to the stirring solution. The solution was heated at 120° C. for one hour. 8 ml of acetonitrile was added to the viscous oil and stirred. Approximately 1 ml of methanol was added and the solution was stirred vigorously for 30 minutes. The resulting white precipitate was collected by vacuum filtration and was washed with acetonitrile and ether to yield 237 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-[(1-oxoethyl)amino]ethyl]propanamide (AIT-0051) as a white solid upon drying. Yield: 76%

Workup

  1. temperatureThe solution was heated at 120° C. for one hour
  2. stirringthe solution was stirred vigorously for 30 minutes
  3. filtrationThe resulting white precipitate was collected by vacuum filtration
  4. washwas washed with acetonitrile and ether

Sources & evidence

ORD record
ord-ecd7db2a3e6748808916396ac064e041
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

Loading…