Trifluoroacetic acid → HCID 89443621, compound

HRID 1528346Notes

Reaction equation

HRID 1528346 reaction equation
[CH:1]1([CH2:7][CH2:8][N:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:24]/[N:25]=[C:26](\[C:33]3[N:37]([CH3:38])[C:36](=[O:39])[O:35][N:34]=3)/[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:18]=2)C(=O)OC(C)(C)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([CH2:7][CH2:8][NH:9][C:17]2[N:18]=[C:19]([CH2:23][O:24]/[N:25]=[C:26](/[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)\[C:33]3[N:37]([CH3:38])[C:36](=[O:39])[O:35][N:34]=3)[CH:20]=[CH:21][CH:22]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 140660332HCID 140660332, compound

Product 1

HCID 89443621HCID 89443621, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (2-cyclohexylethyl){6-[({[(Z)-(4-methyl-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (100 mg, 0.187 mmol, 1 eq.) in dichloromethane (5 ml) was treated with trifluoroacetic acid (0.144 mL, 1.867 mmol, 10 eq.) and refluxed overnight. The reaction was quenched by addition of NaHCO3 sat. aq. and extracted with EtOAc (3×20 ml). The organics were combined, washed with aq. sat. NaCl, dried over MgSO4 and concentrated. After concentration, the residue was purified by chromatography on silica gel to give 3-[(Z)-[({6-[(2-cyclohexylethyl)amino]pyridin-2-yl}methoxy)imino](phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-one (52 mg, 63% yield).

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction was quenched by addition of NaHCO3 sat. aq.
  3. extractionextracted with EtOAc (3×20 ml)
  4. washwashed with aq. sat. NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. concentrationAfter concentration
  8. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e2805dd8dc0740928a6fb3ece702cb7d
Source dataset
uspto-grants-2015_07
Patent number
US09090600B2

Reaction notes

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