Ammonium formate → HCID 90356970, compound

HRID 55880Notes

Reaction equation

HRID 55880 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH3:11])=[N:8][CH:9]=1)([O-])=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[N:12]1([CH:10]([C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH3:11])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 903570074-[1-(5-Nitro-pyridin-2-yl)-ethyl]-morpholine

Product 1

HCID 90356970HCID 90356970, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound 36 (178 mg, 0.75 mmol) was added to Pd/C (20 mg) in ethanol (5 mL), followed by ammonium formate (237 mg, 3.76 mmol) and the reaction mixture heated to reflux for 1 h. The reaction mixture was filtered through celite and the filtrate evaporated. The residue was dissolved in dichloromethane (20 mL) and washed with saturated sodium bicarbonate (20 mL). The organic phase was passed through a hydrophobic frit and evaporated to give the title compound as a yellow oil (155 mg, quant.; LCMS, Rt=0.32 min (MeOH-FA method), m/z 208 (MH+).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 1 h
  3. filtrationThe reaction mixture was filtered through celite
  4. customthe filtrate evaporated
  5. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  6. washwashed with saturated sodium bicarbonate (20 mL)
  7. customevaporated

Sources & evidence

ORD record
ord-450f68f05a4349028a337f4c53af1daa
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

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