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Ethanol → N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874410
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인쇄 미리보기

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HRID 1874410 반응식
[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:29]=[CH:30][CH:31]=2)[O:13][C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([NH:23]C(=O)OCC)=S)=[N:18][CH:19]=2)=[O:8])=[CH:5][C:4]([CH3:32])=[N:3]1.[Cl-].O[NH3+].C([N:39](CC)C(C)C)(C)C.C(O)C>O.CO>[NH2:23][C:21]1[N:20]=[C:17]2[CH:16]=[CH:15][C:14]([O:13][C:12]3[CH:11]=[C:10]([NH:9][C:7]([C:6]4[N:2]([CH3:1])[N:3]=[C:4]([CH3:32])[CH:5]=4)=[O:8])[CH:31]=[CH:30][CH:29]=3)=[CH:19][N:18]2[N:39]=1
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참가 물질

7

반응물 4

HCID 702EthanolHCID 21645Hydroxylamine HClHCID 81531DiisopropylethylamineHCID 57749218ethyl ({[5-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenoxy)pyridin-2-yl]amino}carbonothioyl)carbamate

생성물 1

HCID 57749195N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide수율 69%

시약·촉매·용매

2
HCID 887Methanol용매HCID 962Water용매

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온도
80 °C

실험 절차

A mixture of ethyl ({[5-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenoxy)pyridin-2-yl]amino}carbonothioyl)carbamate (238 mg, 0.524 mmol), hydroxylammonium chloride (364 mg, 5.24 mmol), N,N-diisopropylethylamine (548 μL, 3.14 mmol), ethanol (3 mL) and methanol (3 mL) was stirred at 60° C. for 5 hr and at 80° C. for 2 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate/methanol=50/50/0→40/100/0→40/90/10) and recrystallized from ethyl acetate-hexane to give the title compound (131 mg, 69%) as a white solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate/methanol=50/50/0→40/100/0→40/90/10)
  7. customrecrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-4b1c3a9d6e184bd08b554bb8a3b5bef2
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08304557B2

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