Potassium Carbonate → HCID 117667312, compound

HRID 712666Notes

Reaction equation

HRID 712666 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:22](=[N:23][CH:24]=2)[N:21]([C:25]([NH:27]C(=O)C2C=CC=CC=2)=[O:26])[CH2:20][CH2:19][CH2:18]3)[CH:12]=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CCO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:22](=[N:23][CH:24]=2)[N:21]([C:25]([NH2:27])=[O:26])[CH2:20][CH2:19][CH2:18]3)[CH:12]=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 117667367HCID 117667367, compound

Product 1

HCID 117667312HCID 117667312, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of N-[6-(5-benzyloxy-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carbonyl]-benzamide (620 mg, 1.3 mmol) in EtOH (23 ml) is added potassium carbonate (276 mg, 2.0 mmol). The resultant mixture is heated at reflux for 15 min. After cooling to rt, the solid is removed by filtration and the filtrate is concentrated under vacuum. The residue is dissolved in DCM, washed with water and brine, and is dried (Na2SO4). The solvent is evaporated and the crude product is purified by silica gel column to afford 6-(5-benzyloxy-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (188 mg).

Workup

  1. temperatureat reflux for 15 min
  2. customthe solid is removed by filtration
  3. concentrationthe filtrate is concentrated under vacuum
  4. dissolutionThe residue is dissolved in DCM
  5. washwashed with water and brine
  6. dry with materialis dried (Na2SO4)
  7. customThe solvent is evaporated
  8. customthe crude product is purified by silica gel column

Sources & evidence

ORD record
ord-480fadfbceec4e2086afe51f5b3523dc
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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