Water → 2-Amino-6-(2-furyl)-5-(4-propyl-3-pyridyl)-3-pyridinecarbonitrile

HRID 353230Notes

Reaction equation

HRID 353230 reaction equation
[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:7]([C:15]2[CH:20]=[CH:19][C:18](=O)[NH:17][CH:16]=2)=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH2:28](I)[CH2:29][CH3:30].O>CN(C)C=O>[NH2:1][C:2]1[C:3]([C:4]#[N:5])=[CH:6][C:7]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][C:20]=2[CH2:28][CH2:29][CH3:30])=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 99654582-Amino-6-(2-furyl)-5-(6-oxo-1,6-dihydro-3-pyridinyl)nicotinonitrile

Product 1

HCID 227080532-Amino-6-(2-furyl)-5-(4-propyl-3-pyridyl)-3-pyridinecarbonitrileYield 11.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

2-Amino-6-(2-furyl)-5-(6-oxo-1,6-dihydro-3-pyridinyl)nicotinonitrile (20 mg, 0.072 mmol) and potassium carbonate (30 mg, 0.22 mmol) were introduced into a reaction vessel, dissolved in N,N-dimethylformamide (1 mL). Propyl iodide (52 mg, 0.31 mmol) was added thereto, followed by stirring at 70° C. for 18 hours. After the reaction was finished, water was added thereto, and it was extracted with ethyl acetate. After removing the aqueous layer, the organic layer was concentrated and purified by high performance liquid chromatography, to give the title product as a yellow solid (2.6 mg, 11%; 1.8 mg, 7.8%).

Workup

  1. extractionit was extracted with ethyl acetate
  2. customAfter removing the aqueous layer
  3. concentrationthe organic layer was concentrated
  4. custompurified by high performance liquid chromatography

Sources & evidence

ORD record
ord-de97b6d598a847c5be3c3f6f9ddab0ac
Source dataset
uspto-grants-2004_06
Patent number
US06750232B2

Reaction notes

Loading…