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5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene

IP.com Disclosure Number: IPCOM000171290D
Publication Date: 2008-Jun-03
Document File: 3 page(s) / 68K

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5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene

    5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene described according to the following formula:

C13H13N3

Mw: 211 gr/mol

is an intermedaite in preparation process of 7,8,9,10-tetrahydro-6,10-methano-6 H -pyrazino[2,3-h][3]benzazepine, (2 R ,3 R )-2,3-dihydroxybutanedioate.

   The following procedure provides a preparation process of 5,8,14 Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene.

Preparation of 5,8,14 Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9- pentaene:
1. Charged 1-(5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,9- pentaene)-2,2,2-trifluoro-ethanone at 25-30°C.

2. Charged THF (400ml) and 40% Aq glyoxal solution (56.0 ml in 280.0 ml DM water) at 25-30°C.

3. Raised temperature to 55-60°C and maintain for 2 hrs.
4. Checked the progress of reaction by TLC (Note:-starting material should be absent mobile phase MDC: MeOH: 9:1).

5. Cooled the reaction mass to 25-30°C.
6. Charged ethyl acetate (1000ml) and stirred for 20 min.
7. Separated aqueous layer and extracted aqueous layer with ethyl acetate (2X 300 ml).

8. Washed combined organic layer with DM water (3X500 ml).
9. Washed organic layer with brine solution (500 ml).

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10. Distil...