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Tetrahydrofuran → 3-(4-(2-(Fluoro-phenoxy)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine

HRID 1691145
Notes
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Reaction equation

HRID 1691145 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:6][C:7]1[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16]C(Cl)=NO)=CC=1.C([C:27]1[C:28]([NH2:33])=[N:29][CH:30]=[CH:31][CH:32]=1)#C.[CH2:34]([N:36](CC)CC)C>O>[F:6][C:7]1[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:16][C:2]=1[CH2:3][C:4]1[CH:34]=[N:36][O:1][C:5]=1[C:27]1[C:28]([NH2:33])=[N:29][CH:30]=[CH:31][CH:32]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 124225263-Ethynylpyridin-2-amineHCID 72262883(4-(2-Fluoro-phenoxy)-phenyl)acetohydroximoyl chloride

Product 1

HCID 866124583-(4-(2-(Fluoro-phenoxy)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamineYield 37.3%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
60 °C

Procedure

To a tetrahydrofuran (10.0 mL) solution of (4-(2-fluoro-phenoxy)-phenyl)-acetohydroximoyl chloride (290 mg, 1.04 mmol) described in Manufacturing Example 83-1-3 and 3-ethynyl-pyridin-2-ylamine (50.0 mg, 0.423 mmol) described in Manufacturing Example 1-2-3 was added triethylamine (177 μL, 1.27 mmol) at room temperature, which was stirred for 30 minutes at 60° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5) to obtain the title compound (57.0 mg, 37.3%).

Workup

  1. extractionwhich was then extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5)

Sources & evidence

ORD record
ord-bd95a5d9f74245d29b565618d6f0afdd
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08153662B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes