Trifluoroacetic acid → HCID 67451767, compound

HRID 869205Notes

Reaction equation

HRID 869205 reaction equation
C([O:3][C:4]([C:6]1[N:11]=[N:10][C:9]([N:12]([CH2:20][C:21]2([C:25]3[C:30]([F:31])=[CH:29][CH:28]=[CH:27][N:26]=3)[CH2:24][CH2:23][CH2:22]2)C(=O)OC(C)(C)C)=[CH:8][CH:7]=1)=[CH2:5])C.Cl/[C:33](=[N:39]/O)/[C:34]([O:36][CH2:37][CH3:38])=[O:35].C(O)(C(F)(F)F)=O>C1COCC1>[F:31][C:30]1[C:25]([C:21]2([CH2:20][NH:12][C:9]3[N:10]=[N:11][C:6]([C:4]4[O:3][N:39]=[C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:5]=4)=[CH:7][CH:8]=3)[CH2:24][CH2:23][CH2:22]2)=[N:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetateHCID 68231869HCID 68231869, compound

Product 1

HCID 67451767HCID 67451767, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To t-butyl 6-(1-ethoxyvinyl)pyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate (439 mg, 1.02 mmol) in THF (5.0 mL) was added (E)-ethyl 2-chloro-2-(hydroxyimino)acetate (465 mg, 3.06 mmol) and TEA (1.4 mL, 10.2 mmol). The reaction mixture was stirred at rt for 30 min followed by addition of TFA (5 mL) and then heated to reflux overnight. The mixture was then concentrated and purified by reverse phase chromatography to give 415 mg of the title compound as a colorless oil, LRMS (M+H+) m/z 398.3.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationThe mixture was then concentrated
  4. custompurified by reverse phase chromatography

Sources & evidence

ORD record
ord-2f0c03ff8e1a4ff2bf5e92560640ed69
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

Loading…