Ammonium formate → HCID 86305858, compound

HRID 712625Notes

Reaction equation

HRID 712625 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]([C:13]3[CH:14]=[C:15]4[C:20](=[N:21][CH:22]=3)[N:19]([C:23]([NH2:25])=[O:24])[CH2:18][CH2:17][CH2:16]4)[CH:10]=[N:11][CH:12]=2)[CH2:3][CH2:2]1.C([O-])=O.[NH4+]>[Pd].CO>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]([C:13]3[CH:14]=[C:15]4[C:20](=[N:21][CH:22]=3)[N:19]([C:23]([NH2:25])=[O:24])[CH2:18][CH2:17][CH2:16]4)[CH:10]=[N:11][CH:12]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 117667278HCID 117667278, compound

Product 1

HCID 86305858HCID 86305858, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 6-[5-(3,6-dihydro-2H-pyran-4-yl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (42.0 mg, 0.13 mmol) and 10% Pd/C (42 mg) under Argon is added 2 mL of MeOH. Then ammonium formate (10 eq) is as added and the mixture stirred for 26 hrs at 80° C. The mixture is filtered, concentrated and purified by Preparative HPLC system (10%-80% CH3CN/H2O) to give 31.1 mg of the titled product.

Workup

  1. additionas added
  2. filtrationThe mixture is filtered
  3. concentrationconcentrated
  4. custompurified by Preparative HPLC system (10%-80% CH3CN/H2O)

Sources & evidence

ORD record
ord-e0cda0d7764c48029ff16fd41929408a
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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