1-(3-Aminopropyl)-2-pipecoline → 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[3-(2-methylpiperidin-1-yl)propyl]propanamide

HRID 1534934Notes

Reaction equation

[CH3:1][CH:2]1[N:7]([CH2:8][CH2:9][CH2:10][NH2:11])[CH2:6][CH2:5][CH2:4][CH2:3]1.[O:12]=[C:13]1[NH:21][CH:20]=[N:19][C:18]2[N:17]([CH2:22][CH2:23][C:24](OCC)=[O:25])[CH:16]=[N:15][C:14]1=2>C(#N)C>[O:12]=[C:13]1[NH:21][CH:20]=[N:19][C:18]2[N:17]([CH2:22][CH2:23][C:24]([NH:11][CH2:10][CH2:9][CH2:8][N:7]3[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]3[CH3:1])=[O:25])[CH:16]=[N:15][C:14]1=2

Participants

Conditions

Temperature: 120 °C

Procedure

0.565 g (3.62 mmol) of 1-(3-aminopropyl)-2-pipecoline was placed into a 10 ml round bottom flask with a magnetic stirring bar. The flask was heated to 120° C. and 250 mg (1.06 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) was added. The mixture was heated for two hours at 120° C. and was allowed to cool. The resultant light orange viscous oil was treated with 8 ml acetonitrile and was stirred for about 25 min. The solution was filtered and the solid was washed with acetonitrile and then with ether. This yielded 254 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[3-(2-methylpipiridin-1-yl)propyl]propanamide (AIT-0044) as an off-white solid.

Workup

temperatureThe mixture was heated for two hours at 120° C.
temperatureto cool
filtrationThe solution was filtered
washthe solid was washed with acetonitrile

Sources & evidence

ORD record: ord-450ca13e01fc494cbb460ccc97590b09
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05091432

Reaction notes

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