Trifluoroacetic acid → HCID 86670823, compound

HRID 878364Notes

Reaction equation

HRID 878364 reaction equation
C(OC(=O)[N:7]([CH2:25][C:26]#[N:27])[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][C:21]([F:24])([F:23])[F:22])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:24][C:21]([F:22])([F:23])[O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:13]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[NH:7][CH2:25][C:26]#[N:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86670824HCID 86670824, compound

Product 1

HCID 86670823HCID 86670823, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of cyanomethyl-[4-(2-trifluoromethoxy-phenyl)-pyridin-3-yl]-carbamic acid tert-butyl ester (185 mg, 0.47 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (1 mL) at 0° C. The reaction mixture was stirred at 25° C. for 2 hours and then concentrated under vacuum. The residue was dissolved in 10 mL aqueous sodium bicarbonate solution and 20 mL CH2Cl2 and the layers were separated. The aqueous layer was extracted again with 10 mL CH2Cl2. The combined organic layer was washed with 20 mL brine, dried over Na2SO4, filtered and concentrated under vacuum. The resulting light yellow solid was pure enough to be used in the next step without further purification (115 mg, 83%). LC-MS (ESI): m/z=294.0 (M+H).

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in 10 mL aqueous sodium bicarbonate solution
  3. custom20 mL CH2Cl2 and the layers were separated
  4. extractionThe aqueous layer was extracted again with 10 mL CH2Cl2
  5. washThe combined organic layer was washed with 20 mL brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto be used in the next step without further purification (115 mg, 83%)

Sources & evidence

ORD record
ord-05d6c2d83d2b42859c9604124a553a0e
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…