Trifluoroacetic acid → HCID 68157220, compound

HRID 243018Notes

Reaction equation

HRID 243018 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:19]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[C:22]2[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:21]=2[N:20]=1)[CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:12]([O:11][CH2:10][CH2:9][C@H:8]([NH2:7])[C:19]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[C:22]2[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:21]=2[N:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157589HCID 68157589, compound

Product 1

HCID 68157220HCID 68157220, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-3-benzyloxy-1-(6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)propyl]carbamic acid tert-butyl ester (546 mg, 1.1 mmol) in DCM (10 mL) was added TFA (5 mL) and the mixture was stirred at RT for 1 h. The volatiles were removed under reduced pressure 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. Colourless oil (355 mg, 86%). LCMS (Method B): RT 1.89 min [M+H]+ 377.3.

Workup

  1. customThe volatiles were removed under reduced pressure
  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 1.89 min [M+H]+ 377.3

Sources & evidence

ORD record
ord-7f1751a24b1a4e8990fa099ee1463f9d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…