Water → 2-Amino-4-[4-(2-methoxyethoxy)phenyl]-6-[(2-methyl-1,3-thiazol-4-yl)methylsulphanyl]pyridine-3,5-dicarbonitrile

HRID 2214975Notes

Reaction equation

HRID 2214975 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[CH2:30][C:31]1[N:32]=[C:33]([CH3:36])[S:34][CH:35]=1.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][CH2:30][C:31]2[N:32]=[C:33]([CH3:36])[S:34][CH:35]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 7363414-(Chloromethyl)-2-methyl-1,3-thiazoleHCID 178496105HCID 178496105, compound

Product 1

HCID 219490892-Amino-4-[4-(2-methoxyethoxy)phenyl]-6-[(2-methyl-1,3-thiazol-4-yl)methylsulphanyl]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 90.5 mg (0.61 mmol) of 4-chloromethyl-2-methyl-1,3-thiazole are then added. The suspension is shaken at RT overnight, and water is added. The precipitate is filtered off with suction and dried at 40° C. under reduced pressure. This gives 88.8 mg (66.2% of theory) of product.

Workup

  1. filtrationThe precipitate is filtered off with suction
  2. customdried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-2920701241f648b9987e8c6abcf27cb2
Source dataset
uspto-grants-2006_09
Patent number
US07109218B2

Reaction notes

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