Tetrahydrofuran → HCID 66707832, compound

HRID 1694190Notes

Reaction equation

HRID 1694190 reaction equation
[C:1]([C:3]1[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].[C:10]1([S:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24]C(Cl)=NO)=CC=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:29]([N:31](CC)CC)[CH3:30].[O:36]1CCCC1>>[C:17]1([S:16][C:10]2[CH:11]=[CH:12][C:13]([CH2:30][C:29]3[CH:2]=[C:1]([C:3]4[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=4)[O:36][N:31]=3)=[CH:14][CH:15]=2)[CH:18]=[CH:23][CH:22]=[CH:21][CH:24]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 124225263-Ethynylpyridin-2-amineHCID 72262853(4-Phenylsulfanylmethyl-phenyl)acetohydroximoyl chloride

Product 1

HCID 66707832HCID 66707832, compoundYield 26%

Procedure

To a tetrahydrofuran (3 mL) solution of 3-ethynyl-pyridin-2-ylamine (50 mg, 0.423 mmol) described in Manufacturing Example 1-2-3 and (4-phenylsulfanylmethyl-phenyl)acetohydroximoyl chloride (197 mg, 0.677 mmol) described in Manufacturing Example 206-1-6 was added triethylamine (147 μL, 1.06 mmol), which was stirred for 18 hours at room temperature. The mixture was cooled to room temperature and partitioned into ethyl acetate and water. The organic layer was separated, washed with water, 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:heptane=1:4 to 1:2) to obtain the title compound (41 mg, 26%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4 to 1:2)

Sources & evidence

ORD record
ord-6ecd240bdd86413485da721386113f04
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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