Trifluoroacetic acid → HCID 68157938, compound

HRID 243011Notes

Reaction equation

HRID 243011 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:11]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[C:14]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:13]=2[N:12]=1)[CH2:9][CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:26][C:23]1[CH:24]=[CH:25][C:13]2[N:12]=[C:11]([C@@H:8]([NH2:7])[CH2:9][CH3:10])[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[C:14]=2[CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157088HCID 68157088, compound

Product 1

HCID 68157938HCID 68157938, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)propyl]carbamic acid tert-butyl ester (557 mg, 1.5 mmol) in DCM (8 mL) was added TFA (4 mL) and the mixture stirred at RT for 1 h. The volatiles were removed in vacuo and the resulting residue loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined and concentrated in vacuo. The crude material was used in the following step without further purification. Yellow oil (349 mg, 86%). LCMS (Method B): RT 1.75 min [M+H]+ 270.92.

Workup

  1. customThe volatiles were removed in vacuo
  2. washThe cartridge was washed with MeOH
  3. concentrationconcentrated in vacuo
  4. customThe crude material was used in the following step without further purification
  5. customRT 1.75 min [M+H]+ 270.92

Sources & evidence

ORD record
ord-45c9635529434b9ca11913cc8444d77a
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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