Diisopropylethylamine → HCID 9926083、化合物

HRID 1355362ノート

反応式

HRID 1355362 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 9926083HCID 9926083、化合物収率 18%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-4f4090cbcddd4cd3a98e22f64cc23a91
出典データセット
uspto-grants-2003_07
特許番号
US06586422B2

反応ノート

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