1-(3-Aminopropyl)-2-pyrrolidinone → Ait-034
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=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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%