Trifluoroacetic acid → HCID 68157537, compound

HRID 243264Notes

Reaction equation

HRID 243264 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH2:15][CH3:16])[C:13]2[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[C:18]([F:21])[CH:19]=[CH:20][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:15]([N:14]1[C:13]2[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[C:18]([F:21])[CH:19]=[CH:20][C:12]=2[N:11]=[C:10]1[C@@H:8]([NH2:7])[CH3:9])[CH3:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157441HCID 68157441, compound

Product 1

HCID 68157537HCID 68157537, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(S)-1-(1-Ethyl-6-fluoro-7-pyridin-2-yl-1H-benzoimidazol-2-yl)ethyl]-carbamic acid tert-butyl ester (0.65 g, 1.7 mmol) was added to 20% TFA in DCM (10 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 MeOH and the product eluted with 2M NH3/MeOH then concentrated in vacuo to give title compound as a light yellow gum (0.42 g, 88%). LCMS (Method B): RT 1.65 min [M+H]+ 285.1

Workup

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

Sources & evidence

ORD record
ord-4bf26e1ef36b4f87aebd1cd62922994c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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