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

HRID 384630Notes

Reaction equation

HRID 384630 reaction equation
O.[Sn](Cl)Cl.[C:5]([C:7]1[N:8]=[CH:9][C:10]([NH:13][C:14]2[CH:19]=[C:18]([NH:20][CH2:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]3)[C:17]([N+:35]([O-])=O)=[CH:16][N:15]=2)=[N:11][CH:12]=1)#[N:6]>C(O)C>[NH2:35][C:17]1[C:18]([NH:20][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)=[CH:19][C:14]([NH:13][C:10]2[CH:9]=[N:8][C:7]([C:5]#[N:6])=[CH:12][N:11]=2)=[N:15][CH:16]=1

Participants

4

Reactant 2

HCID 43835034Tin dichloride dihydrateHCID 66746238Tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-nitropyridin-4-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 59613544Tert-butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylateYield 91.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Tin (II) chloride hydrate (678 mg, 5 eq) was added to a solution of tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-nitropyridin-4-ylamino)methyl)piperidine-1-carboxylate (273 mg) in ethanol (20 mL). The mixture was heated at 70° C. for 30 minutes then cooled to room temperature and evaporated to dryness. The residue was diluted with ethyl acetate and saturated aqueous sodium hydrogen carbonate. The suspension was filtered and the aqueous phase was separated and extracted twice with ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated to give crude tert-butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (233 mg) as a yellow solid.

Workup

  1. temperaturethen cooled to room temperature
  2. customevaporated to dryness
  3. additionThe residue was diluted with ethyl acetate and saturated aqueous sodium hydrogen carbonate
  4. filtrationThe suspension was filtered
  5. customthe aqueous phase was separated
  6. extractionextracted twice with ethyl acetate
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-186a22e5dca84f219013e78b48374251
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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