Dimethylformamide → Diisopropylethylamine

HRID 1355349Notes

Reaction equation

HRID 1355349 reaction equation
S1[C:5]2=CC=[CH:8][CH:9]=[N:10][C:4]2=[CH:3]C1.CN(C)C=O.[C:16](#N)[CH3:17].[C:19](=O)([O-])[O-].[K+].[K+]>CS(C)=O.CC(C)=O>[CH:16]([N:10]([CH:4]([CH3:3])[CH3:5])[CH2:9][CH3:8])([CH3:17])[CH3:19]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 67027098HCID 67027098, compound

Product 1

HCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

Bromo-pyrazines II-4 react with tetrahydro-benzo or thieno-azepine compounds III or their hydrochlorides in solvents like N,N-dimethylformamide, acetonitrile, acetone or dimethylsulfoxide in the presence of a base like potassium carbonate or a tertiary amine like diisopropyl-ethylamine at temperatures between room temperature and 80° C. to form the desired 3-(tetrahydro-benzo- or thieno-azepine-3-yl)-pyrazine-2-carbonitriles I-6. 3-(Tetrahydro-benzo- or thieno-azepine-3-yl)-pyrazine-2-carbonitriles of formula I-7 can be prepared according to scheme 4.

Sources & evidence

ORD record
ord-5f9ad93222d248d18e69e09a4bb2a43f
Source dataset
uspto-grants-2003_07
Patent number
US06586422B2

Reaction notes

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