Diglycolamine → 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(2-hydroxyethoxy)ethyl]propanamide

HRID 1534936Notes

Reaction equation

HRID 1534936 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].[O:8]=[C:9]1[NH:17][CH:16]=[N:15][C:14]2[N:13]([CH2:18][CH2:19][C:20](OCC)=[O:21])[CH:12]=[N:11][C:10]1=2>C(#N)C>[O:8]=[C:9]1[NH:17][CH:16]=[N:15][C:14]2[N:13]([CH2:18][CH2:19][C:20]([NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7])=[O:21])[CH:12]=[N:11][C:10]1=2

Participants

4

Reactant 2

HCID 13578DiglycolamineHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 1361161173-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(2-hydroxyethoxy)ethyl]propanamideYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.500 g (4.76 mmol) of 2-(2-aminoethoxy)ethanol was heated with 0.250 g (1.06 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) in a 10 ml round bottom flask at 120° C. for one hour. The solution was treated with 8 ml of acetonitrile and stirred vigorously for 20 minutes. The white precipitate was obtained by filtration and was washed with acetonitrile and then with ether. Upon drying, 265 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(2-hydroxyethoxy)ethyl]propanamide (AIT-047) as a white solid was obtained. Yield: 85%.

Workup

  1. customThe white precipitate was obtained by filtration
  2. washwas washed with acetonitrile
  3. customUpon drying

Sources & evidence

ORD record
ord-61e85330c6e949098f10f93fff031f68
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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