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

HRID 1959393

Reaktionsgleichung

Reaktionsgleichung von HRID 1959393
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

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 22728543Water ethylacetateLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-1359dd61b4354e79adf8a7df2f1491e3
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410112B2

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