Dimethylformamide → N-(6-(3-(N,4-Dimethylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

HRID 1162433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162433
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([C:18]3[CH:19]=[CH:20][C:21]4[N:22]([CH:24]=[C:25]([NH:27][C:28](=[O:30])[CH3:29])[N:26]=4)[N:23]=3)[CH:15]=[CH:16][CH:17]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:31](=O)([O-])[O-].[K+].[K+].CN(C=O)C.IC>O>[CH3:31][N:11]([C:12]1[CH:13]=[C:14]([C:18]2[CH:19]=[CH:20][C:21]3[N:22]([CH:24]=[C:25]([NH:27][C:28](=[O:30])[CH3:29])[N:26]=3)[N:23]=2)[CH:15]=[CH:16][CH:17]=1)[S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:9])=[O:10]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 44124523N-(6-(3-(4-Methylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

Produkt 1

HCID 44124631N-(6-(3-(N,4-Dimethylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a round-bottomed flask was added N-(6-(3-(4-methylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide (from Example 1, Step 5) (0.027 g, 0.064 mmol), potassium carbonate (0.013 g, 0.096 mmol), DMF (1.0 mL) and iodomethane (0.0044 mL, 0.071 mmol). The mixture was stirred at 25° C. for 14 h, then poured into water and extracted with EtOAc (3×30 mL). The combined extracts were washed with water (2×50 mL) and brine (50 mL) then dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (0 to 3% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as a light-yellow solid. MS (ESI positive ion) m/z: 436 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 10.92 (s, 1H), 8.27 (s, 1H), 8.07 (d, J=9.6 Hz, 1H), 7.97 (d, J=8.4 Hz, 1H), 7.75 (t, J=1.9 Hz, 1H), 7.70 (d, J=9.6 Hz, 1H), 7.52 (t, J=7.9 Hz, 1H), 7.39-7.47 (m, 4H), 7.23 (dd, J=8.0 Hz, 1.4 Hz, 1H), 3.20 (s, 3H), 2.41 (s, 3H), 2.12 (s, 3H).

Aufarbeitung

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined extracts were washed with water (2×50 mL) and brine (50 mL)
  3. dry with materialthen dried (Na2SO4)
  4. concentrationconcentrated onto silica
  5. customPurification by silica gel chromatography (0 to 3% MeOH (2 M in NH3)/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-888df2743b5d4b73a641a7b319d67b38
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820665B2

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