Tetrahydrofuran → 5-(3-(6-Phenoxy-pyridin-3-ylmethyl)-isoxazol-5-yl)-pyridin-2-ylamine

HRID 1691294노트

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HRID 1691294 반응식
O1CCCC1.[C:6]([C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1)#[CH:7].[O:15]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](Cl)=[N:30][OH:31])=[CH:24][N:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>O>[O:15]([C:22]1[N:23]=[CH:24][C:25]([CH2:28][C:29]2[CH:7]=[C:6]([C:8]3[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=3)[O:31][N:30]=2)=[CH:26][CH:27]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 219548275-Ethynylpyridin-2-amineHCID 72262860(2-Phenoxy-pyridin-5-yl)acetohydroximoyl chloride

생성물 1

HCID 592552385-(3-(6-Phenoxy-pyridin-3-ylmethyl)-isoxazol-5-yl)-pyridin-2-ylamine수율 30.2%

시약·촉매·용매 1

HCID 962Water용매

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온도
50 °C

실험 절차

To a tetrahydrofuran (2 mL) solution of 5-ethynyl-pyridin-2-ylamine (30 mg, 0.25 mmol) described in Manufacturing Example 28-1-3 were added (2-phenoxy-pyridin-5-yl)acetohydroximoyl chloride (100 mg, 0.381 mmol) described in Manufacturing Example 40-1-4 and triethylamine (70.8 μL, 0.508 mmol), which was stirred for 8 hours at 50° C. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate) to obtain the title compound (26 mg, 30%).

후처리

  1. extractionwhich was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-b29de8cc213442428c1029686deb49f7
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153662B2

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