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

HRID 1355364Notes

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 12 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 the 3-chloro-5-methyl-6-phenyl-pyrazine-2-carbonitrile. The 3-chloro-5-methyl-6-phenyl-pyrazine-2-carbonitrile was finally treated with 2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride (J. Heterocycl. Chem. 1971, 8(5), 779-83) and N-ethyldiisopropylamine in N,N-dimethylformamide at room temperature to yield the 5-methyl-6-phenyl-3-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-pyrazine-2-carbonitrile as yellow amorphous solid; MS: 341 (M+H)+.

Workup

temperaturewere heated in an aqueous solution

Sources & evidence

ORD record: ord-116d6420f1824b1d9549a93513b69de6
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586422B2

Reaction notes

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