1H-Imidazole-1-propanamine → 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[3-(1-imidazolyl)propyl]propanamide
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[CH:26]=[CH:25][N:24]=[CH:23]1>>[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[CH:26]=[CH:25][N:24]=[CH:23]3)=[O:15])[CH:5]=[N:4][C:3]1=2Participants
Procedure
250 mg (1.06 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl) propionic acid, ethyl ester (AIT-0027) was heated with 500 mg (3.99 mmol) of 1-(3-aminopropyl)-imidazole in a 10 ml round bottom flask at 120° C. for two hours with stirring. The resulting viscous yellow oil was chromatographed on 15 g of silica gel, eluting with 60% methanol/40% ethyl acetate, which yielded a highly viscous colorless oil after evaporation of the solvent. The oil was dissolved in approximately 50 ml of ethyl ether and then methanol was added slowly until a white precipitate formed. The precipitate was collected by vacuum filtration and washed with ethyl ether. The material was dried to yield 200 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[3-(1-imidazolyl)propyl]propanamide (AIT-0037) as a white solid. Yield 66%.
Workup
- customThe resulting viscous yellow oil was chromatographed on 15 g of silica gel
- washeluting with 60% methanol/40% ethyl acetate, which
- customyielded a highly viscous colorless oil
- customafter evaporation of the solvent
- dissolutionThe oil was dissolved in approximately 50 ml of ethyl ether
- additionmethanol was added slowly until a white precipitate
- customformed
- filtrationThe precipitate was collected by vacuum filtration
- washwashed with ethyl ether
- customThe material was dried
Sources & evidence
- ORD record
- ord-4a1aa9bbc0e245c7a933fdf5ae7aee88
- Source dataset
- uspto-grants-1992_02
- Patent number
- US05091432
Reaction notes
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