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

HRID 1162433ノート

反応式

HRID 1162433 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-888df2743b5d4b73a641a7b319d67b38
出典データセット
uspto-grants-2010_10
特許番号
US07820665B2

反応ノート

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