Trifluoroacetic acid → (S)-1-(3-Pyridin-2-yl-3H-imidazo[4,5-b]pyridin-2-yl)ethylamine

HRID 243053Notes

Reaction equation

HRID 243053 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C@H:15]([C:17]1[N:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[N:18]=1)[CH3:16])(C)(C)C>C(Cl)Cl>[N:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[N:25]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[N:18]=[C:17]1[C@@H:15]([NH2:14])[CH3:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157645[(S)-1-(3-Pyridin-2-yl-3H-imidazo[4,5-b]pyridin-2-yl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 68157317(S)-1-(3-Pyridin-2-yl-3H-imidazo[4,5-b]pyridin-2-yl)ethylamineYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20 mL) was added to a solution of [(S)-1-(3-pyridin-2-yl-3H-imidazo[4,5-b]pyridin-2-yl)ethyl]carbamic acid tert-butyl ester (1.10 g, 3.24 mmol) in DCM (10 mL) and stirred for 30 min. The reaction mixture was concentrated in vacuo and the residue purified by chromatography (SiO2 0-10% (2M ammonia in methanol) in DCM) to give the title compound (0.145 g, 19%). LCMS (method H): Rt 0.26 min, [M+H]+ 240.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by chromatography (SiO2 0-10% (2M ammonia in methanol) in DCM)

Sources & evidence

ORD record
ord-365c8720cdfd48c6b9aab6508d0ec4d4
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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