Trifluoroacetic acid → (R)-N-(Piperidin-3-yl)-6-(pyrazolo[1,5-a]pyridin-3-yl)pyrazin-2-amine

HRID 1500763Notes

Reaction equation

HRID 1500763 reaction equation
FC(F)(F)C(O)=O.[N:8]1[N:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]2=[C:10]([C:17]2[N:22]=[C:21]([NH:23][C@@H:24]3[CH2:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]3)[CH:20]=[N:19][CH:18]=2)[CH:9]=1>C(Cl)Cl>[NH:26]1[CH2:27][CH2:28][CH2:29][C@@H:24]([NH:23][C:21]2[CH:20]=[N:19][CH:18]=[C:17]([C:10]3[CH:9]=[N:8][N:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=34)[N:22]=2)[CH2:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86691782(R)-tert-Butyl 3-(6-(pyrazolo[1,5-a]pyridin-3-yl)pyrazin-2-ylamino)piperidine-1-carboxylate

Product 1

HCID 58303584(R)-N-(Piperidin-3-yl)-6-(pyrazolo[1,5-a]pyridin-3-yl)pyrazin-2-amineYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.35 mL, 4.56 mmol) was added to a solution of (R)-tert-butyl 3-(6-(pyrazolo[1,5-a]pyridin-3-yl)pyrazin-2-ylamino)piperidine-1-carboxylate (Preparation 28a, 0.30 g, 0.76 mmol) in methylene chloride (10 mL) and the resulting solution was stirred at ambient temperature overnight and then at 50° C. for additional 24 h. The solvent was then evaporated and the residue was redissolved in methylene chloride and washed with a 10% aqueous sodium hydroxide solution. The organic phase was dried over magnesium sulphate, filtered and the solvent was evaporated. The crude product was purified by flash chromatography (10-15% MeOH/CH2Cl2/NH3) to yield the title compound (0.125 g, 56%) as an oil.

Workup

  1. waitat 50° C. for additional 24 h
  2. customThe solvent was then evaporated
  3. dissolutionthe residue was redissolved in methylene chloride
  4. washwashed with a 10% aqueous sodium hydroxide solution
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe crude product was purified by flash chromatography (10-15% MeOH/CH2Cl2/NH3)

Sources & evidence

ORD record
ord-a55692e892e742e4b000b2d9c65b9dc5
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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