1-(3-Aminopropyl)-2-pyrrolidinone → Ait-034

HRID 1534930Notes

Reaction equation

HRID 1534930 reaction equation
[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([O:15]CC)=O)[CH:5]=[N:4][C:3]1=2.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][C:23]1=[O:27]>C(#N)C>[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([NH:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][C:23]3=[O:27])=[O:15])[CH:5]=[N:4][C:3]1=2

Participants

4

Reactant 2

HCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 135484546Ait-034Yield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

250 mg (1.06 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) was added to a 10 ml round bottom flask equipped with a magnetic stirring bar, reflux condenser, and a CaCL2 drying tube. 452 mg (3.18 mmol) 1-(3-aminopropyl)-2-pyrrolidinone and 1 ml acetonitrile were added. The solution was heated to reflux for 17 hours at which time all of the acetonitrile was evaporated leaving a dark viscous oil. The oil was chromatographed on 15 g silica gel, eluting with 40% methanol/60% ethyl acetate. This procedure gave 185 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[3-(2-oxopyrrolidin-1-yl)propyl]propanamide (AIT-0034) as a pure white solid. Yield: 53%

Workup

  1. customequipped with a magnetic stirring bar
  2. temperaturereflux condenser
  3. customa CaCL2 drying tube
  4. temperatureThe solution was heated
  5. customwas evaporated
  6. customleaving a dark viscous oil
  7. customThe oil was chromatographed on 15 g silica gel
  8. washeluting with 40% methanol/60% ethyl acetate

Sources & evidence

ORD record
ord-959f17625bd44445aff13541ab751cb0
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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