Trifluoroacetic acid → (S)-1-[6-Fluoro-1-(1-methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]ethylamine

HRID 243192Notes

Reaction equation

HRID 243192 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[CH:23]=[N:24][N:25]([CH3:27])[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[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=3)[C:20]=2[CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68158164{(S)-1-[6-fluoro-1-(1-methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester

Product 1

HCID 68157529(S)-1-[6-Fluoro-1-(1-methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]ethylamineYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (10 mL) was added to a solution of {(S)-1-[6-fluoro-1-(1-methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester (0.268 g, 0.75 mmol) in DCM (5 mL) and stirred for 15 minutes. 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 an oil (0.113 g, 59%). LCMS (Method C): RT 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-5f7a8f3911644f36917c05f82a77a34f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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