Dimethyl Sulfoxide → 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(1H-indol-3-yl)ethyl]propanamide
Reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.CS(C)=O.[O:17]=[C:18]1[NH:26][CH:25]=[N:24][C:23]2[N:22]([CH2:27][CH2:28][C:29](OC3C=CC([N+]([O-])=O)=CC=3)=[O:30])[CH:21]=[N:20][C:19]1=2>CC(C)=O>[O:17]=[C:18]1[NH:26][CH:25]=[N:24][C:23]2[N:22]([CH2:27][CH2:28][C:29]([NH:1][CH2:2][CH2:3][C:4]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[NH:6][CH:5]=3)=[O:30])[CH:21]=[N:20][C:19]1=2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
0.700 g (4.37 mmol) of tryptamine were placed into a 50 ml round bottom flask equipped with a magnetic stirring bar. Then 5.0 ml of dimethylsulfoxide were added to dissolve the tryptamine. After all the tryptamine had gone into solution, 1.0 g (3.04 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester (AIT-0081) was added and the flask was sealed with a ground glass stopper. The mixture was stirred at room temperature for five hours. The reaction mixture was poured into 60 ml of acetone. The product was filtered, washed twice with 10 ml of acetone and air dried. The yield of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(1H-indol-3-yl)ethyl]-propanamide (AIT-0072) was 0.813 g. Yield: 48% (Purity 99.3%). mp: 204°-206° C.
Workup
- customequipped with a magnetic stirring bar
- additionwas added
- customthe flask was sealed with a ground glass stopper
- filtrationThe product was filtered
- washwashed twice with 10 ml of acetone and air
- customdried
Sources & evidence
- ORD record
- ord-1d78cf2f9dae4fe885427d5629111442
- Source dataset
- uspto-grants-1992_02
- Patent number
- US05091432
Reaction notes
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