Diisopropylethylamine → 3-amino-6-(4-ethylsulfonylpiperazin-1-yl)-N-phenacyl-pyrazine-2-carboxamide

HRID 1959393ノート

反応式

HRID 1959393 の反応式
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[NH2:12][C:13]1[C:14]([C:30](O)=[O:31])=[N:15][C:16]([N:19]2[CH2:24][CH2:23][N:22]([S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])[CH2:21][CH2:20]2)=[CH:17][N:18]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C.CCOC(C)=O.O>[NH2:12][C:13]1[C:14]([C:30]([NH:2][CH2:3][C:4](=[O:5])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:31])=[N:15][C:16]([N:19]2[CH2:20][CH2:21][N:22]([S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])[CH2:23][CH2:24]2)=[CH:17][N:18]=1

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 667445273-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazine-2-carboxylic acid

生成物 1

HCID 667454513-amino-6-(4-ethylsulfonylpiperazin-1-yl)-N-phenacyl-pyrazine-2-carboxamide収率 67%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 22728543Water ethylacetate溶媒

実験手順

2-amino-1-phenyl-ethanone hydrochloride (136.1 mg, 0.7928 mmol) was added to a solution of 3-amino-6-(4-ethylsulfonylpiperazin-1-yl)pyrazine-2-carboxylic acid (250 mg, 0.7928 mmol) and DIPEA (512.3 mg, 690.4 μL, 3.964 mmol) in CH2Cl2 (3.332 mL) and DMF (833.2 μL) and the resulting solution stirred at room temperature for 1 hour. The reaction was diluted with EtOAc/water and the layers separated. The aqueous layer was extracted further with EtOAc (2×) and the combined organics washed with water (3×), dried (MgSO4) and concentrated in vacuo. The mixture was purified on silica gel by flash column chromatography (100% EtOAc) to afford the product (229 mg, 67% Yield). 1H NMR (CDCl3) d 1.28 (3H, t), 3.06 (2H, q), 3.51-3.53 (4H, m), 3.56-3.59 (4H, m), 4.95 (2H, d), 6.2 (2H, br s), 7.56 (2H, m), 7.68 (1H, m), 8.05 (3H, m), 8.65 (1H, m) ppm; MS (ES+) 433.0

後処理

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted further with EtOAc (2×)
  3. washthe combined organics washed with water (3×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe mixture was purified on silica gel by flash column chromatography (100% EtOAc)

出典と根拠

ORDレコード
ord-1359dd61b4354e79adf8a7df2f1491e3
出典データセット
uspto-grants-2013_04
特許番号
US08410112B2

反応ノート

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