Trifluoroacetic acid → (R)-2-Benzyloxy-1-(6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)ethylamine

HRID 243016Notes

Reaction equation

HRID 243016 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:18]1[N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:21]2[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:20]=2[N:19]=1)[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:11]([O:10][CH2:9][C@H:8]([NH2:7])[C:18]1[N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:21]2[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:20]=2[N:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157510[(R)-2-Benzyloxy-1-(6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 68157884(R)-2-Benzyloxy-1-(6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)ethylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(R)-2-benzyloxy-1-(6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (420 mg, 0.91 mmol) in DCM (6 mL) was added TFA (3 mL) and the mixture stirred at RT for 2 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 (284 mg, 86%). LCMS (Method B): RT 2.16 min [M+H]+ 363.20.

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 2.16 min [M+H]+ 363.20

Sources & evidence

ORD record
ord-f5dbe47e20e440caa71233e6ce5e2c6e
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…