4-(6-Acetylaminomethyl-4-chloropyridin-2-yl)-2-(diaminomethyleneamino)thiazole → 4-(6-(Acetamidomethyl)pyridin-2-yl)-2-guanidinothiazole

HRID 1491892Notes

Reaction equation

HRID 1491892 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]2[N:13]=[C:14]([N:17]=[C:18]([NH2:20])[NH2:19])[S:15][CH:16]=2)[CH:9]=[C:8](Cl)[CH:7]=1)(=[O:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([NH:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]2[N:13]=[C:14]([N:17]=[C:18]([NH2:19])[NH2:20])[S:15][CH:16]=2)[CH:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 189539174-(6-Acetylaminomethyl-4-chloropyridin-2-yl)-2-(diaminomethyleneamino)thiazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 104469404-(6-(Acetamidomethyl)pyridin-2-yl)-2-guanidinothiazoleYield 90.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(6-Acetylaminomethyl-4-chloropyridin-2-y1)-2-(diaminomethyleneamino)thiazole (160 mg) was hydrogenated over 10% palladium on carbon (50% wt) (50 mg) in methanol (5 ml) at atmospheric pressure of hydrogen for 8 hours at ambient temperature. After the catalyst was removed by filtration, the solvent was evaporated in vacuo and the residue was mixed with water. The solution was adjusted to pH 10 with aqueous potassium carbonate and the free base was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo to give 4-(6-acetylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (0.13 g).

Workup

  1. customAfter the catalyst was removed by filtration
  2. customthe solvent was evaporated in vacuo
  3. additionthe residue was mixed with water
  4. extractionthe free base was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-cb825e808ae54b9ea78334b8fa8a6322
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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