Trifluoroacetic acid → HCID 68157013, compound

HRID 242938Notes

Reaction equation

HRID 242938 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:18]([C:19]2[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=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:21]1([CH3:25])[CH:22]=[CH:23][CH:24]=[C:19]([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]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157654HCID 68157654, compound

Product 1

HCID 68157013HCID 68157013, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(3-m-tolyl-3H-imidazo[4,5-b]pyridin-2-yl)ethyl]carbamic acid tert-butyl ester (3.01 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 partitioned between DCM and 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 colourless oil (700 mg, 92% over three steps). LCMS (Method C): RT 1.91 min [M+H]+ 253.2.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe resulting residue partitioned between DCM
  3. extractionThe aqueous phase was extracted with DCM (×3)
  4. dry with materialthe combined organic fractions 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-13223a9c6fa74c3cad82fb08152504dd
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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