Trifluoroacetic acid → HCID 89443439, compound

HRID 2206856Notes

Reaction equation

HRID 2206856 reaction equation
[C:1](/[C:3](=[N:10]\[O:11][CH2:12][C:13]1[N:18]=[C:17]([NH:19]C(=O)OC(C)(C)C)[CH:16]=[CH:15][CH:14]=1)/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:19][C:17]1[N:18]=[C:13]([CH2:12][O:11]/[N:10]=[C:3](/[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)\[C:1]#[N:2])[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 140660333tert-butyl N-[6-[[(Z)-[cyano(phenyl)methylidene]amino]oxymethyl]-2-pyridinyl]carbamate

Product 1

HCID 89443439HCID 89443439, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {6-[({[(Z)-cyano(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (5.4 g, 15.32 mmol, 1 eq.) in DCM (200 ml) was added TFA (17.47 g, 153 mmol, 10 eq.). The solution was refluxed for 12 h. The reaction was quenched by addition of aq. sat. NaHCO3 and extracted with EtOAc (3×50 ml). The organics were combined, dried over MgSO4 and concentrated to give (2Z)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)acetonitrile (3.86g, 89% yield).

Workup

  1. temperatureThe solution was refluxed for 12 h
  2. customThe reaction was quenched by addition of aq. sat. NaHCO3
  3. extractionextracted with EtOAc (3×50 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2a7634e7ddd44e77b4deb9343d31c650
Source dataset
uspto-grants-2016_06
Patent number
US09375010B2

Reaction notes

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