Tin dichloride dihydrate → Tert-butyl 3-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

HRID 556817Notes

Reaction equation

HRID 556817 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][CH2:17][CH:18]3[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]3)[C:13]([N+:31]([O-])=O)=[CH:12][N:11]=2)=[N:7][CH:8]=1)#[N:2].O.[Sn](Cl)Cl>C(O)C>[NH2:31][C:13]1[C:14]([NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]2)=[CH:15][C:10]([NH:9][C:6]2[CH:5]=[N:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=2)=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 43835034Tin dichloride dihydrateHCID 66745665Tert-butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-nitropyridin-4-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 66745373Tert-butyl 3-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylateYield 56.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

tert-Butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-nitropyridin-4-ylamino)methyl)piperidine-1-carboxylate (265 mg, 0.583 mmol) was dissolved in ethanol (20 mL) and tin (II) chloride hydrate (658 mg, 2.92 mmol) was added. The suspension was heated for 30 min at 70° C. Solvents were removed by evaporation and the residue was dissolved in ethyl acetate and aqueous saturated sodium hydrogen carbonate. The mixture was filtered and the residue was washed thoroughly with ethyl acetate. The two phases of the filtrate were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried (Na2SO4) and solvent was removed by evaporation affording tert-butyl 3-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (139 mg, 56%). The crude product was used directly in the next step.

Workup

  1. customSolvents were removed by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. filtrationThe mixture was filtered
  4. washthe residue was washed thoroughly with ethyl acetate
  5. customThe two phases of the filtrate were separated
  6. extractionthe aqueous phase was extracted twice with ethyl acetate
  7. dry with materialThe combined organic phases were dried (Na2SO4) and solvent
  8. customwas removed by evaporation

Sources & evidence

ORD record
ord-15bf9e2bdeb44a4fb164e03af3993e77
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Reaction notes

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