Trifluoroacetic acid → HCID 68158163, compound

HRID 243196Notes

Reaction equation

HRID 243196 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C@H:15]([C:17]1[N:21]([C:22]2[N:23]([CH3:27])[N:24]=[CH:25][CH:26]=2)[C:20]2[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:19]=2[N:18]=1)[CH3:16])(C)(C)C>C(Cl)Cl>[F:32][C:29]1[CH:30]=[CH:31][C:19]2[N:18]=[C:17]([C@@H:15]([NH2:14])[CH3:16])[N:21]([C:22]3[N:23]([CH3:27])[N:24]=[CH:25][CH:26]=3)[C:20]=2[CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157194HCID 68157194, compound

Product 1

HCID 68158163HCID 68158163, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (20 mL) was added to a solution of {(S)-1-[6-fluoro-1-(2-methyl-2H-pyrazol-3-yl)-1H-benzoimidazol-2-yl]-ethyl}carbamic acid tert-butyl ester (0.96 g, 2.67 mmol) in DCM (10 mL) and stirred for 15 min. The reaction mixture was concentrated in vacuo and the residue partitioned between DCM (×3) and saturated aqueous NaHCO3. The combined DCM extracts were dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by chromatography (SiO2, 0-10% (2M ammonia in methanol) in DCM) to give the title compound as a colourless oil (0.69 g, 51%). LCMS (Method C): RT 1.55, 1.72 min [M+H]+ 260.1.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between DCM (×3) and saturated aqueous NaHCO3
  3. dry with materialThe combined DCM extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by chromatography (SiO2, 0-10% (2M ammonia in methanol) in DCM)

Sources & evidence

ORD record
ord-3f366306d0ad43c699cdb6582becf724
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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