Sodium Bicarbonate → 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

HRID 1929977노트

반응식

HRID 1929977 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[CH2:24][CH2:23][CH2:22][N:12]2[C:13]=1[C:14]1[N:15]=[N:16][C:17]([NH:20][NH2:21])=[CH:18][CH:19]=1.[Si:25]([O:32][CH2:33][C:34]([CH3:38])([CH3:37])[CH:35]=O)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Si:25]([O:32][CH2:33][C:34]([C:38]1[N:16]2[N:15]=[C:14]([C:13]3[N:12]4[CH2:22][CH2:23][CH2:24][C:11]4=[N:10][C:9]=3[C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])[CH:19]=[CH:18][C:17]2=[N:20][N:21]=1)([CH3:37])[CH3:35])([C:28]([CH3:29])([CH3:30])[CH3:31])([CH3:26])[CH3:27]

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 106563753-((Tert-butyldimethylsilyl)oxy)-2,2-dimethylpropanalHCID 12217721Iodo benzene diacetateHCID 579298742-(2,4-Difluorophenyl)-3-(6-hydrazinylpyridazin-3-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

생성물 1

HCID 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]pyridazine수율 90.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-(2,4-Difluorophenyl)-3-(6-hydrazinylpyridazin-3-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole (6.00 g, 18.3 mmol, Example #35, Step E) was suspended in DCM (125 μL) then 3-(tert-butyldimethylsilyloxy)-2,2-dimethylpropanal (4.15 g, 19.2 mmol, J. Org. Chem., 2002, 67, 2474-2480) was added. The mixture was stirred at ambient temperature for about 2 h. Iodobenzene diacetate (6.00 g, 18.6 mmol) was added then the mixture was stirred for about 30 min. Saturated aqueous NaHCO3 (150 mL) was added then the layers were separated. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The material was purified by flash chromatography on silica gel with EtOAc as an eluent to give the title compound (8.67 g, 90%): LC/MS (Table 1, Method g) Rt=2.77 min; MS m/z: 525.3.2 (M+H)+.

후처리

  1. stirringthe mixture was stirred for about 30 min
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe material was purified by flash chromatography on silica gel with EtOAc as an eluent

출처 및 근거

ORD 기록
ord-dc01374e1f6a42bfb7a30abde210f0fa
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188083B2

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