Triethylamine → HCID 59255129, compound

HRID 78123Notes

Reaction equation

HRID 78123 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](Cl)=[N:13][OH:14])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[C:16]([C:18]1[C:19]([NH2:25])=[N:20][C:21]([NH2:24])=[CH:22][CH:23]=1)#[CH:17].C(N(CC)CC)C>O1CCCC1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[CH:17]=[C:16]([C:18]3[C:19]([NH2:25])=[N:20][C:21]([NH2:24])=[CH:22][CH:23]=3)[O:14][N:13]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 552816763-Ethynylpyridine-2,6-diamineHCID 72262855(4-Butyl-phenyl)-acetohydroximoyl chloride

Product 1

HCID 59255129HCID 59255129, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (3 mL) solution of (4-butyl-phenyl)-acetohydroximoyl chloride (150 mg, 0.665 mmol) described in Manufacturing Example 70-1-3 and 3-ethynyl-pyridin-2,6-diamine (56.5 mg, 0.424 mmol) described in Manufacturing Example 13-1-3 was added triethylamine (232 μL, 1.66 mmol). This mixture was stirred for 5 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 (heptane: ethyl acetate=1:1˜ethyl acetate) to obtain the title compound (66 mg, 31%).

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 (heptane: ethyl acetate=1:1˜ethyl acetate)

Sources & evidence

ORD record
ord-36c15cbbb1ba47159c32f699834843d9
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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