Trifluoroacetic acid → HCID 18439829, compound

HRID 1394127Notes

Reaction equation

HRID 1394127 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[CH:12]=[C:11]2[NH2:25])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:24][C:20]1[CH:19]=[C:18]([C:13]2[CH:12]=[C:11]([NH2:25])[C:10]3[C:15](=[CH:16][CH:17]=[C:8]([NH2:7])[CH:9]=3)[N:14]=2)[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69202883HCID 69202883, compound

Product 1

HCID 18439829HCID 18439829, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The BOC protecting group was removed by the following procedure. Into a 200 mL round bottom flask equipped with a magnetic stir bar and nitrogen inlet was placed 1.0 g (2.71 mmoles, 1 equiv) of [4-amino-2-(3-chlorophenyl)-quinolin-6-yl]-carbamic acid tert-butyl ester and 60 mL of a 1:2 mixture of trifluoroacetic acid and methylene chloride. The mixture was stirred at room temperature for 3 hrs., then concentrated. The residue was made basic with dilute NaOH solution then extracted with ethyl acetate. The organic layer was washed with NaHO solution, dried over Na2SO4, filtered and concentrated. The residue was crystallized from methylene chloride and hexanes to give 700 mg (95%) of the title compound.

Workup

  1. customThe BOC protecting group was removed by the following procedure
  2. customInto a 200 mL round bottom flask equipped with a magnetic stir bar and nitrogen inlet
  3. concentration, then concentrated
  4. extractionthen extracted with ethyl acetate
  5. washThe organic layer was washed with NaHO solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was crystallized from methylene chloride and hexanes

Sources & evidence

ORD record
ord-af627e6a4ae14840861d18b146600f57
Source dataset
uspto-grants-2008_03
Patent number
US07348340B2

Reaction notes

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