Triethylamine → HCID 59255140, compound

HRID 1691349Notes

Reaction equation

HRID 1691349 reaction equation
[C:1]([C:3]1[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].[F:10][C:11]1[CH:27]=[CH:26][C:14]([CH2:15][C:16]2[O:20][C:19]([CH2:21][C:22](Cl)=[N:23][OH:24])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1.C(N(CC)CC)C>O1CCCC1>[F:10][C:11]1[CH:27]=[CH:26][C:14]([CH2:15][C:16]2[O:20][C:19]([CH2:21][C:22]3[CH:2]=[C:1]([C:3]4[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=4)[O:24][N:23]=3)=[CH:18][CH:17]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 124225263-Ethynylpyridin-2-amineHCID 72262865(5-(4-Fluorobenzyl)-furan-2-yl)acetohydroximoyl chloride

Product 1

HCID 59255140HCID 59255140, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 (5-(4-fluorobenzyl)-furan-2-yl) acetohydroximoyl chloride (181 mg, 0.677 mmol) described in Manufacturing Example 208-1-5 was added triethylamine (147 μL, 1.06 mmol), which was stirred for 19 hours at room temperature. The mixture was 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 (9 mg, 6%).

Workup

  1. customThe mixture was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water
  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:heptane=1:4 to 1:2)

Sources & evidence

ORD record
ord-41815109bc55439c9d330d46579ee947
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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