Tetrahydrofuran → HCID 57626339, compound

HRID 78100Notes

Reaction equation

HRID 78100 reaction equation
O1CCCC1.[F:6][C:7]1[CH:25]=[CH:24][C:10]([CH2:11][O:12][C:13]2[N:18]=[CH:17][C:16]([CH2:19][C:20](Cl)=[N:21][OH:22])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[C:26]([C:28]1[C:29]([NH2:35])=[N:30][C:31]([NH2:34])=[CH:32][CH:33]=1)#[CH:27].C(N(CC)CC)C>O>[F:6][C:7]1[CH:25]=[CH:24][C:10]([CH2:11][O:12][C:13]2[N:18]=[CH:17][C:16]([CH2:19][C:20]3[CH:27]=[C:26]([C:28]4[C:29]([NH2:35])=[N:30][C:31]([NH2:34])=[CH:32][CH:33]=4)[O:22][N:21]=3)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 552816763-Ethynylpyridine-2,6-diamineHCID 72262905(6-(4-Fluoro-benzyloxy)-pyridin-3-yl)acetohydroximoyl chloride

Product 1

HCID 57626339HCID 57626339, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a tetrahydrofuran (10.0 mL) solution of (6-(4-fluoro-benzyloxy)-pyridin-3-yl)-acetohydroximoyl chloride (133 mg, 0.450 mmol) described in Manufacturing Example 58-1-5 and 3-ethynyl-pyridin-2,6-diamine (30.0 mg, 0.225 mmol) described in Manufacturing Example 13-1-3 was added triethylamine (94.1 μL, 0.675 mmol), which was stirred for 3 hours at room temperature. Water was added to the reaction solution at room temperature, which was 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=3:1) to obtain the title compound (67.4 mg, 76.5%).

Workup

  1. extractionwhich was 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=3:1)

Sources & evidence

ORD record
ord-7fb8e88c72f846fb800b1c83a71b7dc7
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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