Methyl iodide → HCID 57917420、化合物

HRID 69244ノート

反応式

HRID 69244 の反応式
[H-].[Na+].[N:3]1[NH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][C:8]([C@@H:12]([C:14]1[N:18]3[N:19]=[C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=1)[CH3:13])=[CH:7]2.CI.[CH2:31](Cl)Cl>C1COCC1.[Cl-].[Na+].O>[CH3:31][N:3]1[C:11]2[C:6](=[CH:7][C:8]([C@@H:12]([C:14]3[N:18]4[N:19]=[C:20]([C:23]5[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=5)[CH:21]=[CH:22][C:17]4=[N:16][CH:15]=3)[CH3:13])=[CH:9][CH:10]=2)[CH:5]=[N:4]1

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 178461646HCID 178461646、化合物

生成物 1

HCID 57917420HCID 57917420、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

To a mixture of NaH (4.8 mg, 0.1 mmol) in THF (0.5 mL) cooled to 0° C. was added (3-[(S)-1-(2H-indazol-5-yl)-ethyl]-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine (Example 195, 34.3 mg, 0.10 mmol). The RM was allowed to warm up to rt and stirred 15 min. Then it was cooled down again and methyliodide (21.3 mg, 0.150 mmol) was added dropwise. The RM was allowed to warm up to rt and stirred for 5 h. It was then taken into DCM and brine, extracted, and the organics were joined dried over MgSO4. The solvent was removed and the residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in EtOAc) to afford the title compound after evaporation of the solvent and drying of the material under vacuum (tR 3.72 min (conditions 3), MH+=358, 1H-NMR in DMSO-d6: 8.35 (s, 1H); 8.03 (d, 1H); 8.00 (s, 1H); 7.94 (s, 1H); 7.73 (s, 1H); 7.70 (s, 1H); 7.52 (d, 1H); 7.45 (d, 1H); 7.43 (d, 1H); 4.73 (q, 1H); 4.74 (s, 3H); 3.89 (s, 3H); 1.77 (d, 3H)).

後処理

  1. temperatureto warm up to rt
  2. temperatureThen it was cooled down again
  3. temperatureto warm up to rt
  4. stirringstirred for 5 h
  5. extractionextracted
  6. dry with materialthe organics were joined dried over MgSO4
  7. customThe solvent was removed
  8. customthe residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in EtOAc)

出典と根拠

ORDレコード
ord-6a7634ad9d40413c85553362341f9d65
出典データセット
uspto-grants-2014_09
特許番号
US08822468B2

反応ノート

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