Ammonium formate → HCID 70976652, compound

HRID 882236Notes

Reaction equation

HRID 882236 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][N:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][N:27]=2)[CH2:6][C@@H:5]1[CH3:35])(=[O:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].C(O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][N:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][N:27]=2)[CH2:6][C@@H:5]1[CH3:35])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 70976544HCID 70976544, compound

Product 1

HCID 70976652HCID 70976652, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a flask charged with ethyl 6-((2S,4R)-1-acetyl-2-methyl-4-((5-nitropyridin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)nicotinate (for a preparation see Intermediate 25)(780 mg, 1.640 mmol), ammonium formate (1034 mg, 16.40 mmol) and palladium on carbon (10% Pd/C) (160 mg, 1.503 mmol) was added ethanol (15 ml) and the resulting mixture was refluxed for 45 min. The reaction was cooled to room temperature, filtered through Celite™, the residue washed with EtOH and the combined filtrate and washings 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; which gave ethyl 6-((2S,4R)-1-acetyl-4-((5-aminopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)nicotinate (450 mg, 1.010 mmol, 61.6% yield) as a pink foam. LCMS (HpH, 2 min), Rt=0.93 min, MH+=446.

Workup

  1. temperaturethe resulting mixture was refluxed for 45 min
  2. filtrationfiltered through Celite™
  3. washthe residue washed with EtOH
  4. concentrationthe combined filtrate and washings concentrated 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-9a974f4e1db647e49bfa3cac43b86486
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

Loading…