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 1930016노트

반응식

HRID 1930016 반응식
[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

참가 물질

4

반응물 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

생성물 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-ol수율 16%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-ae185b3e128b4768b7eb9a45c88e747d
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188083B2

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