Trifluoroacetic acid → 1-(1H-Pyrrolo[2,3-b]pyridin-4-yl)piperidin-4-amine

HRID 1036321Notes

Reaction equation

HRID 1036321 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]3[NH:27][CH:28]=[CH:29][C:22]=23)[CH2:17][CH2:16]1)(C)(C)C>ClCCl>[NH:27]1[C:23]2=[N:24][CH:25]=[CH:26][C:21]([N:18]3[CH2:19][CH2:20][CH:15]([NH2:14])[CH2:16][CH2:17]3)=[C:22]2[CH:29]=[CH:28]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24828978HCID 24828978, compound

Product 1

HCID 115430581-(1H-Pyrrolo[2,3-b]pyridin-4-yl)piperidin-4-amineYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 ml) was added dropwise to a solution of [1-(1H-pyrrolo[2,3-b]pyridin-4-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester (19 mg, 0.06 mmol) in dichloromethane (1 ml), with stirring and cooling on ice. After 2.5 hours, the solvents were concentrated in vacuo and the crude product was purified on a basic resin NH2 cartridge (2 g, 15 ml) eluting with methanol to afford the required compound (12.5 mg, 0.058 mmol, 96%). LC-MS (LCT) Rt 0.95 [M+H]+ 217

Workup

  1. temperaturecooling on ice
  2. concentrationthe solvents were concentrated in vacuo
  3. customthe crude product was purified on a basic resin NH2 cartridge (2 g, 15 ml)
  4. washeluting with methanol

Sources & evidence

ORD record
ord-2d7b6e6df2d44497a76ab6749fb7ae57
Source dataset
uspto-grants-2013_10
Patent number
US08546407B2

Reaction notes

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