Triethylamine → HCID 59255432, compound

HRID 1694084Notes

Reaction equation

HRID 1694084 reaction equation
[CH:1]1([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14](Cl)=[N:15][OH:16])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18]([C:20]1[C:21]([NH2:27])=[N:22][C:23]([NH2:26])=[CH:24][CH:25]=1)#[CH:19].C(N(CC)CC)C>O1CCCC1>[CH:1]1([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]3[CH:19]=[C:18]([C:20]4[C:21]([NH2:27])=[N:22][C:23]([NH2:26])=[CH:24][CH:25]=4)[O:16][N:15]=3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 552816763-Ethynylpyridine-2,6-diamineHCID 72262868HCID 72262868, compound

Product 1

HCID 59255432HCID 59255432, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (3 mL) solution of (4-cyclopentyloxy-phenyl)-acetohydroximoyl chloride (150 mg, 0.592 mmol) described in Manufacturing Example 78-1-4 and 3-ethynyl-pyridin-2,6-diamine (50.3 mg, 0.378 mmol) described in Manufacturing Example 13-1-3 was added triethylamine (206 μL, 1.48 mmol). This reaction mixture was stirred for 1.5 hours at room temperature. This 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 (64 mg, 31%).

Workup

  1. customThis 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-c114706a005741a185d5195917e422f7
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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