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

HRID 2214976

Reaction equation

HRID 2214976 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]([NH2:36])[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]([NH2:36])[S:34][CH:35]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 732294-Chloromethylthiazol-2-ylamineHCID 516892Sodium BicarbonateHCID 178496105HCID 178496105, compound

Product 1

HCID 219490822-Amino-4-[4-(2-methoxyethoxy)phenyl]-6-[(2-amino-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 68.3 mg (0.46 mmol) of 4-chloromethyl-2-amino-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 115.9 mg (86.2% 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-9b4b6d61968440f8b03c91c6bd69902a
Source dataset
uspto-grants-2006_09
Patent number
US07109218B2

Linked notes

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