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

HRID 2214969Notes

Reaction equation

HRID 2214969 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][CH: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:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[S:34][CH:35]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazoleHCID 516892Sodium BicarbonateHCID 178496105HCID 178496105, compound

Product 1

HCID 219490842-Amino-4-[4-(2-methoxyethoxy)phenyl]-6-[(2-phenyl-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 96.4 mg (0.46 mmol) of 4-chloromethyl-2-phenyl-1,3-thiazole 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 149 mg (97% 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-d7b94a00b0cd426a80b1edc6bfdb7044
Source dataset
uspto-grants-2006_09
Patent number
US07109218B2

Reaction notes

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