Triethylamine → HCID 59255140, compound

HRID 1891949Notes

Reaction equation

HRID 1891949 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-361c0934340d48219c839f58a769bedb
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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