Water → 2-Amino-4-(2-bromo-1,3-thiazol-4-yl)-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)pyridine-3,5-dicarbonitrile

HRID 1969476Notes

Reaction equation

HRID 1969476 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[N:11]=[C:12]([Br:15])[S:13][CH:14]=2)[C:5]([C:16]#[N:17])=[C:4]([SH:18])[N:3]=1.Cl[CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[S:24][CH:25]=1.C(=O)(O)[O-].[Na+].O>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[N:11]=[C:12]([Br:15])[S:13][CH:14]=2)[C:5]([C:16]#[N:17])=[C:4]([S:18][CH2:20][C:21]2[N:22]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[S:24][CH:25]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178510491HCID 178510491, compound

Product 1

HCID 668979732-Amino-4-(2-bromo-1,3-thiazol-4-yl)-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)pyridine-3,5-dicarbonitrileYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.78 g (purity 77%, 10.882 mmol) of 2-amino-4-(2-bromo-1,3-thiazol-4-yl)-6-sulfanylpyridine-3,5-dicarbonitrile were initially charged in 30 ml of DMF, 2.923 g (11.971 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 2.742 g (32.647 mmol) of sodium bicarbonate were added and the mixture was stirred at room temperature overnight. The reaction mixture was added to water, and the precipitated solid was filtered off with suction, washed with water and dried under high vacuum. The contaminated product was applied to silica gel and purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1). The product-containing fractions were concentrated, the residue was triturated with dichloromethane and the solid was filtered off, washed with dichloromethane and dried under high vacuum. This gave 1.1 g of the target compound in a purity of 91% (yield: 17% of theory).

Workup

  1. filtrationthe precipitated solid was filtered off with suction
  2. washwashed with water
  3. customdried under high vacuum
  4. custompurified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1)
  5. concentrationThe product-containing fractions were concentrated
  6. customthe residue was triturated with dichloromethane
  7. filtrationthe solid was filtered off
  8. washwashed with dichloromethane
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-c9cba4102400471b958ace2d8c8f215c
Source dataset
uspto-grants-2013_04
Patent number
US08426602B2

Reaction notes

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