Water → 2-Amino-4-[4-(2-methoxyethoxy)phenyl]-6-[(2-pyridinylmethyl)sulphanyl]pyridine-3,5-dicarbonitrile

HRID 2214974Notes

Reaction equation

HRID 2214974 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:12][CH:11]=2)[C:5]([C:21]#[N:22])=[C:4]([SH:23])[N:3]=1.C(=O)(O)[O-].[Na+].Cl.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36]Cl.O>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:14][CH:15]=2)[C:5]([C:21]#[N:22])=[C:4]([S:23][CH2:36][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 23392Picolyl chloride hydrochlorideHCID 516892Sodium BicarbonateHCID 178496105HCID 178496105, compound

Product 1

HCID 219490872-Amino-4-[4-(2-methoxyethoxy)phenyl]-6-[(2-pyridinylmethyl)sulphanyl]pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.31 mmol) of 2-amino-4-[4-(2-methoxyethoxy)phenyl]-6-sulphanyl-pyridine-3,5-dicarbonitrile are dissolved in 1 ml of DMF. 103 mg (1.23 mmol) of sodium bicarbonate and 75.4 mg (0.46 mmol) of 2-picolyl chloride hydrochloride are then added. The suspension is shaken at RT overnight, and water is added. The precipitate is filtered off with suction, washed with ethanol and diethyl ether and dried at 40° C. under reduced pressure. This gives 104 mg (81% of theory) of product.

Workup

  1. filtrationThe precipitate is filtered off with suction
  2. washwashed with ethanol and diethyl ether
  3. customdried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-1f7d840e02bb4d9da166a53d3e85051d
Source dataset
uspto-grants-2006_09
Patent number
US07109218B2

Reaction notes

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