Triethylamine → HCID 59255149, compound

HRID 78248Notes

Reaction equation

HRID 78248 reaction equation
[C:1]([C:3]1[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].[C:10](Cl)(=[N:12][OH:13])[CH3:11].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>O1CCCC1>[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:11][C:10]2[CH:2]=[C:1]([C:3]3[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=3)[O:13][N:12]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 124225263-Ethynylpyridin-2-amineHCID 86612460(4-(Pyridin-2-yloxy)benzene)-acetohydroximoyl chloride

Product 1

HCID 59255149HCID 59255149, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a tetrahydrofuran (5 mL) solution of 3-ethynyl-pyridin-2-ylamine (45 mg, 0.38 mmol) described in Manufacturing Example 1-2-3 and (4-(pyridin-2-yloxy)benzene)-acetohydroximoyl chloride (200 mg, 0.76 mmol) described in Manufacturing Example 209-1-4 was added triethylamine (139 mg, 1.4 mmol), which was stirred for 10 minutes at 60° C. The reaction solution was cooled to room temperature, NH silica gel was added, and the solvent was evaporated under a reduced pressure. The crude product that had adsorbed to the NH silica gel was purified by NH silica gel column chromatography (heptane:ethyl acetate=2:1, 1:1) to obtain the title compound (40 mg, 30%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. additionNH silica gel was added
  3. customthe solvent was evaporated under a reduced pressure
  4. customwas purified by NH silica gel column chromatography (heptane:ethyl acetate=2:1, 1:1)

Sources & evidence

ORD record
ord-6d548ce2181a4f5e82aef2f203448390
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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