1-Amino-2-propanol → HCID 136116419, compound

HRID 1534942Notes

Reaction equation

HRID 1534942 reaction equation
[CH3:1][CH:2]([OH:5])[CH2:3][NH2:4].[O:6]=[C:7]1[NH:15][CH:14]=[N:13][C:12]2[N:11]([CH2:16][CH2:17][C:18](OCC)=[O:19])[CH:10]=[N:9][C:8]1=2>C(#N)C>[O:6]=[C:7]1[NH:15][CH:14]=[N:13][C:12]2[N:11]([CH2:16][CH2:17][C:18]([NH:4][CH2:3][CH:2]([OH:5])[CH3:1])=[O:19])[CH:10]=[N:9][C:8]1=2

Participants

4

Reactant 2

HCID 41-Amino-2-propanolHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 136116419HCID 136116419, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

0.500 g (6.66 mmol) DL-1-amino-2-propanol and 0.250 (1.06 mmol) 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) were heated together in a 10 ml round bottom flask with stirring at 120° C. for one hour. The solution was allowed to cool to room temperature and 10 ml acetonitrile was added and the solution was stirred. The solution was triturated with a small amount of methanol (approximately 1 ml) and was stirred until the appearance of a fine white precipitate. The solution was filtered and the white solid was washed with acetonitrile and then with ether. Upon drying, 240 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-(2-hydroxypropyl)propanamide (AIT-0059) as a white solid was obtained. Yield: 85%. m.p. -212°-216° C.

Workup

  1. temperatureto cool to room temperature
  2. stirringthe solution was stirred
  3. customThe solution was triturated with a small amount of methanol (approximately 1 ml)
  4. stirringwas stirred until the appearance of a fine white precipitate
  5. filtrationThe solution was filtered
  6. washthe white solid was washed with acetonitrile
  7. customUpon drying

Sources & evidence

ORD record
ord-0c6c0eaef4334ba0a1b33ff0965e9ec2
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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