Triethylamine → HCID 178425179, compound

HRID 1501158Notes

Reaction equation

HRID 1501158 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH:8]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][N:11]=2)[CH3:9])[CH:2]=1.C(N(CC)CC)C.[NH2:26][CH2:27][C:28]1[C:29]([OH:36])=[N:30][C:31]([CH3:35])=[CH:32][C:33]=1[CH3:34]>ClCCl>[OH:36][C:29]1[C:28]([CH2:27][NH:26][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][C:10]([CH:8]([O:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH3:9])=[N:11][CH:12]=2)=[C:33]([CH3:34])[CH:32]=[C:31]([CH3:35])[N:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89581490HCID 89581490, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425179HCID 178425179, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(1-(Pridin-3-yloxy)ethyl)nicotinic acid (150 mg, 0.61 mol) was dissolved in dichloromethane (20 mL), H-benzo[d][1,2,3]triazol-1-ol (124 mg, 0.92 mmol), 1-(3-dmethylaminopropyl)-3-ethylcarbodiimide hydrochloride (176 mg, 0.92 mmol) and triethylamine (3 mL, 1.84 mmol) were added. After stirring at room temperature for 10 minutes, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (93 mg, 0.61 mmol) was added. The mixture was stirred at room temperature for 18 hours. Once the start material was consumed, water (30 mL) was added. The mixture was extracted with dichloromethane (40 mL). The organic layer was separated and concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=15/1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-6-(1-(pyridin-3-yloxy)ethyl)nicotinamide (50 mg, 21.5%).

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. customOnce the start material was consumed
  3. additionwater (30 mL) was added
  4. extractionThe mixture was extracted with dichloromethane (40 mL)
  5. customThe organic layer was separated
  6. concentrationconcentrated
  7. customto give a residue
  8. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=15/1)

Sources & evidence

ORD record
ord-19d66ae040e34358ab0970e655a864c2
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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