Trifluoroacetic acid → HCID 68158146, compound

HRID 243268Notes

Reaction equation

HRID 243268 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH:15]2[CH2:18][CH:17]([C:19]#[N:20])[CH2:16]2)[C:13]2[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@H:8]([C:10]1[N:14]([CH:15]2[CH2:18][CH:17]([C:19]#[N:20])[CH2:16]2)[C:13]2[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:12]=2[N:11]=1)[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68158133HCID 68158133, compound

Product 1

HCID 68158146HCID 68158146, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{(S)-1-[1-(3-Cyanocyclobutyl)-6-fluoro-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester (0.21 g, 0.586 mmol) was added to 20% TFA in DCM (7 mL) and the resultant solution stirred at 20° C. for 1 hour. The reaction mixture was concentrated in vacuo and the residue loaded onto an Isolute® SCX-2 cartridge which was washed with DCM and MeOH, then the product was eluted with 2M NH3/MeOH and concentrated in vacuo to give title compound as a colourless solid (0.076 g, 51%). LCMS (Method J): RT 1.52 min [M+H]+ 259

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwas washed with DCM and MeOH
  3. washthe product was eluted with 2M NH3/MeOH
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-799995dde3de447fbf90299540226a45
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…