COELENTERAZINE 400 A synthesis
- Product Name:COELENTERAZINE 400 A
- CAS Number:70217-82-2
- Molecular formula:C26H21N3O
- Molecular Weight:391.46
Yield:70217-82-2 80%
Reaction Conditions:
Stage #1: benzylglyoxal;2-amino-3-benzyl-5-phenyl-pyrazine in ethanol; for 0.333333 h;Inert atmosphere;
Stage #2: with hydrogenchloride in ethanol;water; for 18 h;Reflux;
Steps:
11.I
2,8-Dibenzyl-6-phenyl-7H-imidazo[1,2-a]pyrazin-3-one (Coelenterazine HH). A solution of 2-amino-3-benzyl-5-phenylpyrazine20 (2.0 g, 8.0 mmol) and 2-oxo-3-phenyl-propionaldehyde (3.0 g, 16 mmol) in ethanol (125 mL) was deoxygenated with argon gas for 20 min. To the solution was added concentrated hydrochloric acid (4.0 mL) and the reaction mixture was heated at reflux for 18 h. The reaction was allowed to cool to ambient temperature and then evaporated to a brown solid. The crude product was triturated with ethanol (40 mL) and the resulting solid material was collected by centrifugation and then dried in a vacuum oven to afford 1.28 g (41%) of the desired compound. This product was 80% pure according to HPLC analysis
References:
US7692022,2010,B2 Location in patent:Page/Page column 46
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