Water → 3-{5-Amino-3-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-pyrazol-1-yl}-phenol

HRID 1402436노트

반응식

HRID 1402436 반응식
C([O:8][C:9]1[CH:10]=[C:11]([N:15]2[C:19]([NH2:20])=[CH:18][C:17]([C:21]([CH3:42])([CH3:41])[CH2:22][O:23][Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:16]2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:20][C:19]1[N:15]([C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=2)[N:16]=[C:17]([C:21]([CH3:42])([CH3:41])[CH2:22][O:23][Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:18]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 2723923Ammonium formateHCID 866872842-(3-Benzyloxy-phenyl)-5-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-2H-pyrazol-3-ylamine

생성물 1

HCID 866872853-{5-Amino-3-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-pyrazol-1-yl}-phenol수율 52%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A solution of Intermediate 153c (1.21 g, 2.1 mmol) in ethanol (IMS grade, 20 mL) was treated with water (1 mL) and ammonium formate (1.33 g, 21 mmol). The mixture was purged with N2 then 10% Pd/C (0.67 g, 0.63 mmol Pd) was added. The mixture was heated to reflux for 1 h then filtered through celite and the filtrate was concentrated in vacuo. The residue was partitioned between EtOAc and water. The phases were separated and the aqueous layer was extracted with EtOAc (×2). The combined organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by FCC, using 0-40% EtOAc in cyclohexane, to give the title compound (0.53 g, 41% over 2 steps) as a golden gum. LCMS (Method 3): Rt 4.55 min, m/z 486.5 [MH+].

후처리

  1. customThe mixture was purged with N2
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 1 h
  4. filtrationthen filtered through celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was partitioned between EtOAc and water
  7. customThe phases were separated
  8. extractionthe aqueous layer was extracted with EtOAc (×2)
  9. washThe combined organic phase was washed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by FCC

출처 및 근거

ORD 기록
ord-7aaacffc8b38410aa7092a1e1d868aa3
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08907094B2

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