Trifluoroacetic acid → HCID 178424320, compound

HRID 1890353Notes

Reaction equation

HRID 1890353 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][C:9]1[N:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[N+:16]([O-])=O.[CH3:19]OC(OC)OC.C(O)(C(F)(F)F)=O>CO.[Ni]>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[N:8]1[C:9]2=[N:14][C:13]([OH:15])=[CH:12][CH:11]=[C:10]2[N:16]=[CH:19]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9005Trimethyl orthoformateHCID 178424357HCID 178424357, compound

Product 1

HCID 178424320HCID 178424320, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

6-(2-Methylcyclohexylamino)-5-nitropyridin-2-ol (100 mg, 0.398 mmol) and nickel (11.68 mg, 0.199 mmol) in MeOH (10 mL) were stirred at 22° C. for 24 hr under H2. After filtration through Celite®, the solution was concentrated in the presence of a few drops of TFA. The residue was dissolved in trimethoxymethane (2112 mg, 19.90 mmol) and stirred overnight with a drop of TFA. The mixture was concentrated. The residue was diluted with water, neutralized with NaHCO3 solution and extracted with EtOAC. The EtOAc extract was concentrated and the residue was purified by column chromatography to give the title compound as a brown oil (37 mg). LCMS m/z=232.10 [M+H]+, 1H NMR (400 MHz, CDCl3) major isomer; δ ppm 0.75 (d, J=6.3 Hz, 3H), 1.22-2.20 (m, 9H), 4.18-4.27 (m, 1H), 6.89 (d, J=8.9 Hz, 1H), 8.17 (d, J=8.9 Hz, 1H), 8.52 (s, 1H).

Workup

  1. filtrationAfter filtration through Celite®
  2. concentrationthe solution was concentrated in the presence of a few drops of TFA
  3. concentrationThe mixture was concentrated
  4. additionThe residue was diluted with water
  5. extractionextracted with EtOAC
  6. extractionThe EtOAc extract
  7. concentrationwas concentrated
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c4e249139ef0495ab0c87fb44e9ec88d
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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