Diisopropylethylamine → HCID 9926083, compound

HRID 1355362Notes

Reaction equation

HRID 1355362 reaction equation
Cl[C:2]1[C:3]([C:11]#[N:12])=[N:4][C:5]([CH2:9][CH3:10])=[C:6]([CH3:8])[N:7]=1.ClC1C(C#N)=NC(C)=C(CC)N=1.Cl.[CH2:26]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[CH2:30][CH2:29][NH:28][CH2:27]1.C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH2:9]([C:5]1[N:4]=[C:3]([C:11]#[N:12])[C:2]([N:28]2[CH2:27][CH2:26][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[CH2:30][CH2:29]2)=[N:7][C:6]=1[CH3:8])[CH3:10]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 111596793-Chloro-5-ethyl-6-methyl-2-pyrazinecarbonitrileHCID 11355861HCID 11355861, compoundHCID 170652302,3,4,5-Tetrahydro-1H-3-benzazepine--hydrogen chloride (1/1)

Product 1

HCID 9926083HCID 9926083, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.300 g (1.65 mmol) of the 1:1 mixture of the 3-chloro-6-ethyl-5-methyl-pyrazine-2 -carbonitrile and the 3-chloro-5-ethyl-6-methyl-pyrazine-2-carbonitrile, of 0.395 g (1.30 mmol) of 2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride (J. Heterocycl. Chem. 1971, 8(5), 779-83) and of 0.566 g (2.60 mmol) of N-ethyl-diisopropylamine in 1.0 ml of N,N-dimethylformamide was stirred at room temperature for 60 hours and then at 60° C. for 18 hours. The reaction mixture was subsequently poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of ethylacetate. The combined ethylacetate phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was then chromatographed on silica gel using dichloromethane as eluent giving 0.086 g (0.29 mmol, 18% of theory) of the 6-ethyl-5-methyl-3-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-pyrazine-2-carbonitrile as yellowish solid after crystallization from dichlormethane/pentane; MS: 293 (M+H)+; and 0.074 g (0.25 mmol, 15% of theory) of the 5-ethyl-6-methyl-3-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-pyrazine-2-carbonitrile as yellowish solid; MS: 293 (M+H)+.

Workup

  1. extractionextracted 3 times with 50 ml of ethylacetate
  2. dry with materialThe combined ethylacetate phases were dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue formed
  5. customwas then chromatographed on silica gel

Sources & evidence

ORD record
ord-4f4090cbcddd4cd3a98e22f64cc23a91
Source dataset
uspto-grants-2003_07
Patent number
US06586422B2

Reaction notes

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