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

HRID 242974Notes

Reaction equation

HRID 242974 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12]2[C:13]([N:18]=1)=[N:14][CH:15]=[CH:16][CH:17]=2)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:19]1([N:11]2[C:12]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[N:18]=[C:10]2[C@@H:8]([NH2:7])[CH3:9])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157945[(S)-1-(1-Phenyl-1H-imidazo[4,5-b]pyridin-2-yl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 68157105(S)-1-(1-Phenyl-1H-imidazo[4,5-b]pyridin-2-yl)ethylamineYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(1-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)ethyl]carbamic acid tert-butyl ester (910 mg, 2.69 mmol) in DCM (5 mL) was added TFA (15 mL) and the mixture stirred at RT for 15 min. The volatiles were removed in vacuo and the resulting residue dissolved in DCM and washed with a saturated aqueous solution of NaHCO3. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) to afford the title compound as a brown solid (340 mg, 53%). 1H NMR (CDCl3, 400 MHz): δ 8.55 (1H, dd, J=4.78, 1.56 Hz), 7.65-7.53 (3H, m), 7.45-7.37 (3H, m), 7.15 (1H, dd, J=8.04, 4.78 Hz), 4.18 (1H, q, J=6.71 Hz), 3.49 (2H, s), 1.48 (3H, d, J=6.71 Hz).

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe resulting residue dissolved in DCM
  3. washwashed with a saturated aqueous solution of NaHCO3
  4. extractionThe aqueous phase was further extracted with DCM (×3)
  5. dry with materialthe combined organic fractions dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-4cef7a9703c34fc5b8673e9ceae6901c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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