Trifluoroacetic acid → HCID 68157412, compound

HRID 242799Notes

Reaction equation

HRID 242799 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:19]1([N:18]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=[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 68157612HCID 68157612, compound

Product 1

HCID 68157412HCID 68157412, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)ethyl]carbamic acid tertbutyl ester (1.77 g) in DCM (4 mL) was added TFA (20 mL) and the resulting mixture was stirred at RT for 15 min. Volatiles were removed under reduced pressure and the resulting residue was partitioned between DCM and a saturated solution of NaHCO3. The aqueous phase was further extracted with DCM and then the combined organic layers were dried (Na2SO4) and then concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% 2M NH3/MeOH in DCM) affording (S)-1-(3-Phenyl-3H-imidazo[4,5-b]pyridin-2-yl)ethylamine as colourless gum (540 mg, 20% over three steps). LCMS: RT 1.65 min [M−NH2]+ 222.0.

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe resulting residue was partitioned between DCM
  3. extractionThe aqueous phase was further extracted with DCM
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-f15f04b777b64724a15148e97d3692fc
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…