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Tetrahydrofuran → HCID 59255162, compound

HRID 1694078
Notes
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Reaction equation

HRID 1694078 reaction equation
O1CCCC1.[C:6]([C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[CH:12][CH:13]=1)#[CH:7].[F:16][C:17]1[CH:18]=[C:19]([CH:32]=[CH:33][CH:34]=1)[O:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27][C:28](Cl)=[N:29][OH:30])=[CH:23][CH:22]=1.C(N(CC)CC)C>O>[F:16][C:17]1[CH:18]=[C:19]([CH:32]=[CH:33][CH:34]=1)[O:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27][C:28]2[CH:7]=[C:6]([C:8]3[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[CH:12][CH:13]=3)[O:30][N:29]=2)=[CH:23][CH:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 552816763-Ethynylpyridine-2,6-diamineHCID 72262903(6-(3-Fluoro-phenoxy)-pyridin-3-yl)-acetohydroximoyl chloride

Product 1

HCID 59255162HCID 59255162, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
50 °C

Procedure

To a tetrahydrofuran (2 mL) solution of 3-ethynyl-pyridin-2,6-diamine (10 mg, 75 mmol) described in Manufacturing Example 13-1-3 and (6-(3-fluoro-phenoxy)-pyridin-3-yl)-acetohydroximoyl chloride (42 mg, 0.15 mmol) described in Manufacturing Example 71-1-4 was added triethylamine (21 μL, 0.15 mmol), which was stirred for 1 hour at 50° C. under nitrogen atmosphere. Water was added at room temperature 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:methanol=20:1) to obtain the title compound (27 mg, 95%).

Workup

  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:methanol=20:1)

Sources & evidence

ORD record
ord-f0cebd8246aa43fcb1bf9294d1c184dd
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08158657B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes