HCID 131731819、化合物 → (Rac)-3-[1-(6-fluoro-1-methyl-1h-indazol-5-yl)-ethyl]-6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

HRID 69280ノート

反応式

HRID 69280 の反応式
ClC1C=CC2N(C(C(C3C=[C:15]4[C:19](=CC=3F)[N:18]([CH3:23])[N:17]=[CH:16]4)=O)=CN=2)N=1.Cl[C:25]1[CH:26]=[CH:27][C:28]2[N:29]([C:31]([C:34]([C:37]3[CH:38]=[C:39]4[C:43](=[CH:44][C:45]=3[F:46])[N:42]([CH3:47])[N:41]=[CH:40]4)(O)[CH3:35])=[CH:32][N:33]=2)[N:30]=1.C[Mg]Br>C1COCC1.CCOC(C)=O>[F:46][C:45]1[CH:44]=[C:43]2[C:39]([CH:40]=[N:41][N:42]2[CH3:47])=[CH:38][C:37]=1[CH:34]([C:31]1[N:29]2[N:30]=[C:25]([C:15]3[CH:16]=[N:17][N:18]([CH3:23])[CH:19]=3)[CH:26]=[CH:27][C:28]2=[N:33][CH:32]=1)[CH3:35]

参加物

5

反応物 2

HCID 131731819HCID 131731819、化合物HCID 178418573HCID 178418573、化合物

生成物 1

HCID 57917432(Rac)-3-[1-(6-fluoro-1-methyl-1h-indazol-5-yl)-ethyl]-6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(rac)-1-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(6-fluoro-1-methyl-1H-indazol-5-yl)-ethanol (6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(6-fluoro-1-methyl-1H-indazol-5-yl)-methanone (Stage 278.3, 3.7 g, 11.22 mmol) was dissolved in THF (250 mL) with heating under Argon. The solution was let to cool down and methylmagnesium bromide (3 M, 7.48 mL) was added. The mixture was stirred at rt for 1 h. It was then diluted with EtOAc and washed with a saturated NaHCO3 sol. The aqueous phase was extracted twice with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (CombiFlash® Companion System®, with 120 g RediSep® silica gel column, DCM/MeOH=100:0->94:6 in 20 min). The collected fractions containing product were evaporated and the residue was dried under vacuum to afford the title compound (tR 1.14 min (conditions 2), MH+=346)

後処理

  1. temperaturewith heating under Argon
  2. temperatureto cool down
  3. washwashed with a saturated NaHCO3 sol. The aqueous phase
  4. extractionwas extracted twice with EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (CombiFlash® Companion System®, with 120 g RediSep® silica gel column, DCM/MeOH=100:0->94:6 in 20 min)
  10. additionThe collected fractions containing product
  11. customwere evaporated
  12. customthe residue was dried under vacuum

出典と根拠

ORDレコード
ord-1b9959746a904c50a3dcd7cc5ce05d70
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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