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

HRID 2401537Notes

Reaction equation

HRID 2401537 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-a42557f2cda14e3cbc8106f85e5a80ef
Source dataset
uspto-grants-2014_08
Patent number
US08796293B2

Reaction notes

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