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tert-Butanol → Tert-butyl [6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate

HRID 2391189
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HRID 2391189 반응식
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=1)[O:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH:19]=[C:20](C(O)=O)[N:21]=2)[N:18]=1)=[O:7].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:40])C=CC=CC=1.C([N:52]([CH2:55]C)CC)C.[C:57]([OH:61])([CH3:60])([CH3:59])[CH3:58]>C(OCC)(=O)C>[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=1)[O:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH:19]=[C:20]([NH:52][C:55](=[O:40])[O:61][C:57]([CH3:60])([CH3:59])[CH3:58])[N:21]=2)[N:18]=1)=[O:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 573875936-(3-{[3-(Trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazine-2-carboxylic acid

생성물 1

HCID 57387816Tert-butyl [6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate수율 39%

시약·촉매·용매

1
HCID 8857Ethyl Acetate용매

실험 절차

A suspension of 6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazine-2-carboxylic acid (111 mg, 0.25 mmol), diphenylphosphoryl azide (103 mg, 0.375 mmol), triethylamine (51 mg, 0.5 mmol) and tert-butanol (5.0 mL) was stirred at room temperature for 5 min, heated to 100° C. and stirred overnight. After allowing the reaction mixture to cool to room temperature, ethyl acetate was added to the mixture, and the mixture was washed with saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/19→ethyl acetate alone) to give the title compound (79 mg, 39%) as a white solid.

후처리

  1. temperatureheated to 100° C.
  2. stirringstirred overnight
  3. temperatureto cool to room temperature
  4. washthe mixture was washed with saturated aqueous sodium hydrogencarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/19→ethyl acetate alone)

출처 및 근거

ORD 기록
ord-24fb434191e44aa7b02b517b37e6f555
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08273741B2

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