1-Phenyl-1,2-propanedione → HCID 69035433, compound

HRID 1838206Notes

Reaction equation

[C:1]1([C:7](=O)[C:8](=O)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:12][CH:13]([C:17]([NH2:19])=[O:18])[C:14]([NH2:16])=[O:15]>>[CH3:9][C:8]1[NH:16][C:14](=[O:15])[C:13]([C:17]([NH2:19])=[O:18])=[N:12][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 113631-Phenyl-1,2-propanedione

HCID 964572-Aminopropanediamide

Product 1

HCID 69035433HCID 69035433, compound

Procedure

In analogy to the procedure described in example 75a-c, 1-phenyl-1,2-propanedione and 2-aminomalonamide were heated in an aqueous solution to give 5-methyl-3-oxo-6-phenyl-3,4-dihydro-pyrazine-2-carboxylic acid amide. Then, the 5-methyl-3-oxo-6-phenyl-3,4-dihydro-pyrazine-2-carboxylic acid amide was treated with triethylamine and phosphorus pentachloride in phosphorus oxychloride at reflux to give 3-chloro-5-methyl-6-phenyl-pyrazine-2-carbonitrile. The 3-chloro-5-methyl-6-phenyl-pyrazine-2-carbonitrile was finally treated with 1-(4-fluorophenyl)piperazine and N-ethyldiiso-propyl-amine in N,N-dimethylformamide at room temperature to yield the 4-(4-fluoro-phenyl)-6′-methyl-5′-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-carbonitrile as yellow solid; m.p. 117-120° C.; MS: 374 (M+H)+.

Workup

temperaturewere heated in an aqueous solution

Sources & evidence

ORD record: ord-f64c924bc5a1421e85e5b1044429e507
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673795B2

Reaction notes

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