Diisopropylethylamine → HCID 9881094, compound

HRID 1355366Notes

Reaction equation

HRID 1355366 reaction equation
Cl[C:2]1[C:3]([C:15]#[N:16])=[N:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6]([CH3:8])[N:7]=1.Cl.[CH2:18]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][CH2:21][NH:20][CH2:19]1.C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH3:8][C:6]1[N:7]=[C:2]([N:20]2[CH2:19][CH2:18][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][CH2:21]2)[C:3]([C:15]#[N:16])=[N:4][C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 170652302,3,4,5-Tetrahydro-1H-3-benzazepine--hydrogen chloride (1/1)HCID 18753299HCID 18753299, compound

Product 1

HCID 9881094HCID 9881094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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)+.

Sources & evidence

ORD record
ord-52453f4439124bf68e06a05feb88ecb4
Source dataset
uspto-grants-2003_07
Patent number
US06586422B2

Reaction notes

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