Trifluoroacetic acid → HCID 18510678, compound

HRID 2219089Notes

Reaction equation

HRID 2219089 reaction equation
FC(F)(F)C(O)=O.CC(C)(OC([N:14]([CH:22]([C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]([CH:38]2[O:42][N:41]=[C:40]([C:43]3[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=3)[CH2:39]2)=[O:37])=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)C(=O)OC(C)(C)C)=O)C>C(Cl)Cl>[NH2:14][CH:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:29]1[CH:30]=[CH:31][C:32]([NH:35][C:36]([CH:38]2[O:42][N:41]=[C:40]([C:43]3[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=3)[CH2:39]2)=[O:37])=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69920798HCID 69920798, compound

Product 1

HCID 18510678HCID 18510678, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

) Trifluoroacetic acid (50 ml) was added dropwise to a solution of compound (125) (0.037 mol) in CH2Cl2 (500 ml), stirred at RT. The reaction mixture was stirred overnight at RT. The solvent was evaporated under reduced pressure. Toluene was added and azeotroped on the rotary evaporator (2×). The residue (crude oil) was dissolved in CH2Cl2. The organic solution was washed with 1 N NaOH (2×), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was crystallized from EtOAc, filtered off, washed with EtOAc, then dried, yielding 7.4 g (54%) of (±)-N-[4-(aminophenylmethyl)phenyl]-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxamide. (compound 126)

Workup

  1. stirringThe reaction mixture was stirred overnight at RT
  2. customThe solvent was evaporated under reduced pressure
  3. additionToluene was added
  4. customazeotroped on the rotary evaporator (2×)
  5. dissolutionThe residue (crude oil) was dissolved in CH2Cl2
  6. washThe organic solution was washed with 1 N NaOH (2×)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was crystallized from EtOAc
  11. filtrationfiltered off
  12. washwashed with EtOAc
  13. customdried

Sources & evidence

ORD record
ord-5c3eadb26a9d4138a8537fec4e44ceab
Source dataset
uspto-grants-2008_08
Patent number
US07414048B2

Reaction notes

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