Tetrabutylammonium Fluoride → 2-(6-(2-(2,4-Difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)-2-methylpropan-1-ol

HRID 1930016ノート

反応式

HRID 1930016 の反応式
[Si]([O:8][CH2:9][C:10]([C:13]1[N:17]2[N:18]=[C:19]([C:22]3[N:26]4[CH2:27][CH2:28][CH2:29][C:25]4=[N:24][C:23]=3[C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=3[F:37])[CH:20]=[CH:21][C:16]2=[N:15][N:14]=1)([CH3:12])[CH3:11])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:37][C:31]1[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:30]=1[C:23]1[N:24]=[C:25]2[CH2:29][CH2:28][CH2:27][N:26]2[C:22]=1[C:19]1[CH:20]=[CH:21][C:16]2[N:17]([C:13]([C:10]([CH3:12])([CH3:11])[CH2:9][OH:8])=[N:14][N:15]=2)[N:18]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 579299783-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-6-(2-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[4,3-b]pyridazine

生成物 1

HCID 498309602-(6-(2-(2,4-Difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)-2-methylpropan-1-ol収率 16%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The 3-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-6-(2-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[4,3-b]pyridazine (0.606 g, 1.16 mmol, Preparation #E.1.1.1) was dissolved in THF (15 mL) and reacted at about ambient temperature with TBAF (1.0 M in THF, 1.39 mL, 1.39 mmol) for about 4 h. The crude reaction mixture was partitioned between water and DCM. The organics were dried over MgSO4, filtered and concentrated under reduced pressure. The resulting crude material was purified by chromatography on silica gel (DCM/MeOH gradient from 100:0-85:15) and triturated with a mixture of heptane/Et2O (90:10) to give the title compound as a yellow solid (0.074 g, 16%): LC/MS (Table 1, Method g) Rt=1.64 min.; MS m/z: 411.98 (M+H)+.

後処理

  1. customThe crude reaction mixture
  2. customwas partitioned between water and DCM
  3. dry with materialThe organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude material was purified by chromatography on silica gel (DCM/MeOH gradient from 100:0-85:15)
  7. customtriturated with a mixture of heptane/Et2O (90:10)

出典と根拠

ORDレコード
ord-ae185b3e128b4768b7eb9a45c88e747d
出典データセット
uspto-grants-2012_05
特許番号
US08188083B2

反応ノート

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