Sodium Bicarbonate → 2-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-4-(methylthio)pyridine-3,5-dicarbonitrile

HRID 1913498Notes

Reaction equation

HRID 1913498 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([S:10][CH3:11])[C:5]([C:12]#[N:13])=[C:4]([SH:14])[N:3]=1.C(=O)(O)[O-].[Na+].Cl[CH2:21][C:22]1[N:23]=[C:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[S:25][CH:26]=1>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([S:10][CH3:11])[C:5]([C:12]#[N:13])=[C:4]([S:14][CH2:21][C:22]2[N:23]=[C:24]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[S:25][CH:26]=2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178503294HCID 178503294, compound

Product 1

HCID 666721182-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-4-(methylthio)pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.30 g (32.84 mmol) of the compound from Example 43A (2-amino-6-mercapto-4-(methylthio)pyridine-3,5-dicarbonitrile), 11.03 g (131.36 mmol) of sodium bicarbonate and 9.62 g (39.41 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole were combined in 150 ml of absolute DMF and stirred at room temperature for 12 h. A solid precipitated out; this solid was filtered off with suction through a glass frit and washed three times with water and twice with diethyl ether. The residue was dried under reduced pressure.

Workup

  1. customA solid precipitated out
  2. filtrationthis solid was filtered off with suction through a glass frit
  3. washwashed three times with water
  4. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-aa8afd188e0b4fa48bfb7a7fd57407b7
Source dataset
uspto-grants-2013_12
Patent number
US08609686B2

Reaction notes

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