Potassium Carbonate → HCID 117667239, compound

HRID 712633Notes

Reaction equation

HRID 712633 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[N:12][C:13]2[NH:14][CH2:15][CH2:16][CH2:17][C:18]=2[CH:19]=1.[C:21]([N:29]=C=O)(=[O:28])C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[C:21]([N:14]1[C:13]2[N:12]=[CH:11][C:10]([C:5]3[CH:6]=[N:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:2])=[O:20])=[CH:19][C:18]=2[CH2:17][CH2:16][CH2:15]1)(=[O:28])[NH2:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 117666971HCID 117666971, compound

Product 1

HCID 117667239HCID 117667239, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-isonicotinic acid methyl ester (131 mg, 0.49 mmol) in DCM (30 mL) is added benzoyl isocyanate (107 mg, 0.73 mmol). The mixture is heated to reflux for 3 hrs. The solvent is then removed and the residue is dissolved in anhydrous MeOH (10 mL). Then K2CO3 (180 mg, 1.3 mmol) is added and the mixture is heated to reflux for 0.5 h. After cooling down, the organic solvent is evaporated. The residue is dissolved in water and washed with DCM. The water layer is separated and purified by neutral preparative HPLC to give 80 mg of 3-(8-carbamoyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-isonicotinic acid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 3 hrs
  3. customThe solvent is then removed
  4. dissolutionthe residue is dissolved in anhydrous MeOH (10 mL)
  5. temperaturethe mixture is heated
  6. temperatureto reflux for 0.5 h
  7. temperatureAfter cooling down
  8. customthe organic solvent is evaporated
  9. dissolutionThe residue is dissolved in water
  10. washwashed with DCM
  11. customThe water layer is separated
  12. custompurified by neutral preparative HPLC

Sources & evidence

ORD record
ord-48534b8300014daf8cc46560d7662171
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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