Diisopropylethylamine → 2-(3-Benzyloxy-phenyl)-5-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-2H-pyrazol-3-ylamine

HRID 1402435노트

반응식

HRID 1402435 반응식
[C:1]([Si:5]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O:6][CH2:7][C:8]([CH3:15])([CH3:14])[C:9](=O)[CH2:10][C:11]#[N:12])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([NH:43][NH2:44])[CH:40]=[CH:41][CH:42]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCN(C(C)C)C(C)C>C(O)C.CCOC(C)=O>[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([N:43]2[C:11]([NH2:12])=[CH:10][C:9]([C:8]([CH3:15])([CH3:14])[CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:44]2)[CH:40]=[CH:41][CH:42]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 12891839(3-(Benzyloxy)phenyl)hydrazine hydrochlorideHCID 866872835-(tert-Butyl-diphenyl-silanyloxy)-4,4-dimethyl-3-oxo-pentanenitrile

생성물 1

HCID 866872842-(3-Benzyloxy-phenyl)-5-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-2H-pyrazol-3-ylamine수율 107%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of Intermediate 153b (1.00 g, 2.63 mmol) in ethanol (IMS grade, 20 mL) was treated with 3-benzyloxyphenylhydrazine hydrochloride (0.66 mL, 2.63 mmol) then DIPEA (0.46 mL, 2.63 mmol) and the mixture was heated to reflux for 114 h. The cooled reaction mixture was diluted with EtOAc and a saturated aqueous sodium bicarbonate solution and the mixture was filtered and the phases separated. The aqueous layer was extracted with EtOAc (×2) and the combined organic phase was washed with brine, dried (Na2SO4), and concentrated in vacuo to give an orange oil (1.62 g). The gum was purified by FCC, using 0-20% EtOAc in cyclohexane, to give the title compound as a yellow oil (1.21 g, 80%). LCMS (Method 3): Rt 5.40 min, m/z 576.5 [MH+].

후처리

  1. temperatureto reflux for 114 h
  2. customThe cooled reaction mixture
  3. filtrationa saturated aqueous sodium bicarbonate solution and the mixture was filtered
  4. customthe phases separated
  5. extractionThe aqueous layer was extracted with EtOAc (×2)
  6. washthe combined organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ab7ff027d2114b4bafc6028532e7fc43
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08907094B2

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