Trifluoroacetic acid → HCID 58278853, compound

HRID 85157Notes

Reaction equation

HRID 85157 reaction equation
C(OC([NH:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67203742Benzyl 4-((6-(tert-butoxycarbonylamino)pyridin-3-yl)methyl)piperazine-1-carboxylate

Product 1

HCID 58278853HCID 58278853, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 4-((6-(tert-butoxycarbonylamino)pyridin-3-yl)methyl)piperazine-1-carboxylate (104; 2.20 g, 5.20 mmol) in dichloromethane (10 mL) was added TFA (3.4 g, 31.2 mmol) at room temperature. The resulting reaction mixture was stirred at room temperature for 12 h and then concentrated under reduced pressure. Enough saturated aqueous Na2CO3 was added to adjust the pH=9. The resulting mixture was then extracted with dichloromethane (3×25 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to afford benzyl 4-((6-aminopyridin-3-yl)methyl)piperazine-1-carboxylate 105 (1.50 g, 89%).

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated under reduced pressure
  3. additionEnough saturated aqueous Na2CO3 was added
  4. extractionThe resulting mixture was then extracted with dichloromethane (3×25 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c841c797173d4fa4830ac3fba9e1d989
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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