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

HRID 242898Notes

Reaction equation

HRID 242898 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:11]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[N:12]=1)[CH2:9][CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:20]1([N:19]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[N:12]=[C:11]2[C@@H:8]([NH2:7])[CH2:9][CH3:10])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157696[(S)-1-(3-Phenyl-3H-imidazo[4,5-b]pyridin-2-yl)propyl]carbamic acid tert-butyl ester

Product 1

HCID 68157876(S)-1-(3-Phenyl-3H-imidazo[4,5-b]pyridin-2-yl)propylamineYield 48.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)propyl]carbamic acid tert-butyl ester (1.27 g, 3.60 mmol) in DCM (25 mL) was added TFA (10 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 solution of NaHCO3. The aqueous phase was 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 0-8% 2M NH3/MeOH in DCM) to afford the title compound as a brown oil (440 mg, 40% over 3 steps). 1H NMR (CDCl3, 400 MHz): δ 8.34 (1H, d, J=4.82 Hz), 8.08 (1H, d, J=8.00 Hz), 7.67-7.52 (3H, m), 7.45 (2H, d, J=7.60 Hz), 7.30-7.22 (1H, m), 3.99 (1H, t, J=6.70 Hz), 2.02-1.87 (1H, m), 1.83-1.69 (3H, m), 0.89 (3H, t, J=7.40 Hz).

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe resulting residue dissolved in DCM
  3. washwashed with a saturated solution of NaHCO3
  4. extractionThe aqueous phase was 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 0-8% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-35dd999b19b5453a8b8bb2056f96b15f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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