Triethylamine → HCID 18753299, compound

HRID 1355365Notes

Reaction equation

HRID 1355365 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=O)[C:5]([C:14]([NH2:16])=O)=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.P(Cl)(Cl)(Cl)(Cl)[Cl:26]>P(Cl)(Cl)(Cl)=O>[Cl:26][C:4]1[C:5]([C:14]#[N:16])=[N:6][C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:2]([CH3:1])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24819Phosphorus pentachlorideHCID 69035433HCID 69035433, compound

Product 1

HCID 18753299HCID 18753299, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

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

  1. temperatureat reflux

Sources & evidence

ORD record
ord-2bccc3a5fd9f4c5084744240fd617eff
Source dataset
uspto-grants-2003_07
Patent number
US06586422B2

Reaction notes

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