Trifluoroacetic acid → HCID 22479144, compound

HRID 1392184Notes

Reaction equation

HRID 1392184 reaction equation
C(OC([N:8]1[N:15]2[C:11]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=3)([C:12](=[O:25])[N:13]([C:17]3[CH:22]=[C:21]([Cl:23])[N:20]=[C:19]([Cl:24])[CH:18]=3)[C:14]2=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:33]([C:30]1[CH:29]=[CH:28][C:27]([CH2:26][C:11]23[CH2:10][CH2:9][NH:8][N:15]2[C:14](=[O:16])[N:13]([C:17]2[CH:22]=[C:21]([Cl:23])[N:20]=[C:19]([Cl:24])[CH:18]=2)[C:12]3=[O:25])=[CH:32][CH:31]=1)#[N:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22479214HCID 22479214, compound

Product 1

HCID 22479144HCID 22479144, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound from Example 56 (102 mg) in CH2Cl2 (5 mL) at −10° C. was added TFA (1 mL). After warming to room temperature, the reaction mixture was stirred for a total of 1 hour while monitoring the progress by TLC. Upon consumption of the starting material, the reaction mixture was cooled to 0° C. and DIEA (4.5 mL) was added carefully. After 2 hours, water (20 mL) and EtOAc (30 mL) were added and the mixture shaken. The aqueous phase was then separated and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by liquid chromatography (SiO2, EtOAc) and re-crystallization from EtOAc/hexanes to give the titled compound (62 mg). MS (m/z) 402 (M); mp 187° C.

Workup

  1. customUpon consumption of the starting material
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. additionDIEA (4.5 mL) was added carefully
  4. waitAfter 2 hours
  5. additionwater (20 mL) and EtOAc (30 mL) were added
  6. stirringthe mixture shaken
  7. customThe aqueous phase was then separated
  8. extractionextracted with EtOAc
  9. dry with materialThe combined organic layers were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by liquid chromatography (SiO2, EtOAc) and re-crystallization from EtOAc/hexanes

Sources & evidence

ORD record
ord-435f0f4145704491b921ca49f0d03168
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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