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

HRID 2214977Notes

Reaction equation

HRID 2214977 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]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)[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]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[S:34][CH:35]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 21201002-[4-(Chloromethyl)-1,3-thiazol-2-yl]pyridineHCID 178496105HCID 178496105, compound

Product 1

HCID 219490792-Amino-4-[4-(2-methoxyethoxy)phenyl]-6-[(2-(2-pyridyl)-1,3-thiazol-4-yl)methylsulphanyl]pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.15 mmol) of 2-amino-4-[4-(2-methoxyethoxy)phenyl]-6-sulphanyl-pyridine-3,5-dicarbonitrile are dissolved in 1 ml of DMF. 51.5 mg (0.61 mmol) of sodium bicarbonate and 58.6 mg (0.23 mmol) of 4-chloromethyl-2-(2-pyridyl)-1,3-thiazole are then added. The suspension is shaken 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 67.4 mg (87.9% 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-63ffd2364e7147f591eef71d72acaafb
Source dataset
uspto-grants-2006_09
Patent number
US07109218B2

Reaction notes

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