3-Amino-1,2-propanediol → HCID 136096310, compound

HRID 1534944Notes

Reaction equation

HRID 1534944 reaction equation
[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[O:7]=[C:8]1[NH:16][CH:15]=[N:14][C:13]2[N:12]([CH2:17][CH2:18][C:19](OCC)=[O:20])[CH:11]=[N:10][C:9]1=2>C(#N)C.CO>[O:7]=[C:8]1[NH:16][CH:15]=[N:14][C:13]2[N:12]([CH2:17][CH2:18][C:19]([NH:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5])=[O:20])[CH:11]=[N:10][C:9]1=2

Participants

4

Reactant 2

HCID 735613-Amino-1,2-propanediolHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 136096310HCID 136096310, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 21959252Acetonitrile methanolSolvent

Conditions

Temperature
110 °C

Procedure

0.500 g (5.49 mmol) of 3-amino-1,2-propanediol was placed into a 10 ml round bottom flask with a magnetic stirring bar. The flask was heated to 110° 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 stirred at 100°-110° C. for one hour. The flask was allowed to cool to room temperature and 10 ml of 1:1 acetonitrile/methanol was added and the solution was stirred vigorously for 30 minutes. The resulting white precipitate was collected using Buchner funnel filtration to yield 272 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-(2,3-dihydroxyprop-1-yl)propanamide (AIT-0062) as a white solid. 91% yield.

Workup

  1. temperatureto cool to room temperature
  2. stirringthe solution was stirred vigorously for 30 minutes
  3. customThe resulting white precipitate was collected
  4. filtrationBuchner funnel filtration

Sources & evidence

ORD record
ord-e694f2beebe9494c824cdb20e435b92a
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

Loading…