ChemicalBook CAS DataBase List 2-(2,9-diazabicyclo[4.3.0]nona-2,4,7,10-tetraen-7-yl)ethanamine

2-(2,9-diazabicyclo[4.3.0]nona-2,4,7,10-tetraen-7-yl)ethanamine synthesis

12synthesis methods

Product Name:2-(2,9-diazabicyclo[4.3.0]nona-2,4,7,10-tetraen-7-yl)ethanamine
CAS Number:4649-12-1
Molecular formula:C9H11N3
Molecular Weight:161.2

1H-Pyrrolo[2,3-b]pyridine, 3-(2-nitroethyl)-

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2-(2,9-diazabicyclo[4.3.0]nona-2,4,7,10-tetraen-7-yl)ethanamine

4649-12-1
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Yield: 99.6 g

Reaction Conditions:

with 20% palladium hydroxide-activated charcoal;hydrogen in ethanol at 70; for 16 h;

Steps:

6 Example 6 2-(1H-pyrrolo[2,3-b]pyridine-3-yl)ethanamine
The compound (114.9 g) produced in Example 5 was suspended in ethanol (1.15 L), and 20% palladium hydroxide/carbon (50% hydrous product, 57.7 g) was added. The mixture was stirred on a water bath at 70° C. for about 8 hours under the hydrogen atmosphere. After a temperature was returned to room temperature, the reaction was allowed to stand overnight under the nitrogen atmosphere, hydrogen replacement operation was performed again, and the reaction was stirred on a water bath at 70° C. for about 8 hours under the hydrogen atmosphere. After a temperature was returned to room temperature, a catalyst was filtered off using Celite. The filtrate was concentrated under reduced pressure to obtain the title compound (99.6 g) having the following physical property values.; TLC: Rf 0.14 (chloroform:methanol:water=90:10:1);¹H-NMR (CDCl₃): δ 2.89 (t, J=6.5 Hz, 2H) 3.01 (t, J=7.0 Hz, 2H) 7.07 (dd, J=8.00, 5.00 Hz, 1H) 7.15 (s, 1H) 7.92 (dd, J=8.00, 1.50 Hz, 1H) 8.29 (dd, J=5.00, 1.50 Hz, 1H) 10.12 (s, 1H).

References:

ONO PHARMACEUTICAL CO., LTD.;Ohata, Akira;Nakatani, Shingo;Sugiyama, Tetsuya;Morimoto, Takashi US2013/109699, 2013, A1 Location in patent:Paragraph 0929-0932

90929-74-1 Synthesis