Ammonium formate → HCID 70976489, compound

HRID 882233Notes

Reaction equation

HRID 882233 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][N:26]=2)[CH2:6][C@@H:5]1[CH3:34])(=[O:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][N:26]=2)[CH2:6][C@@H:5]1[CH3:34])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 70976485HCID 70976485, compound

Product 1

HCID 70976489HCID 70976489, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a flask charged with methyl 4-((2S,4R)-1-acetyl-2-methyl-4-((5-nitropyridin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (for a preparation see Intermediate 20)(2.43 g, 5.28 mmol), ammonium formate (3.33 g, 52.8 mmol) and palladium on carbon (0.562 g, 5.28 mmol) was added MeOH (50 mL) and the resulting mixture was refluxed for 30 min. The reaction was cooled to room temperature, filtered through Celite™ and the residue washed with MeOH then DMF. The methanolic filtrate and washings were combined and concentrated in vacuo. The residue was dissolved in EtOAc, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography eluting with a MeOH/DCM gradient to give methyl 4-((2S,4R)-1-acetyl-4-((5-aminopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (2.0 g, 4.65 mmol, 88% yield) as a dark pink foam. LCMS (HpH, 2 min), Rt=0.94 min, MH+=431.

Workup

  1. temperaturethe resulting mixture was refluxed for 30 min
  2. filtrationfiltered through Celite™
  3. washthe residue washed with MeOH
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography
  10. washeluting with a MeOH/DCM gradient

Sources & evidence

ORD record
ord-8b01e38f7f474d02b381b19148255536
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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