Potassium Carbonate → HCID 86305668, compound

HRID 712601Notes

Reaction equation

HRID 712601 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][C:13]3[NH:14][CH2:15][CH2:16][CH2:17][C:18]=3[CH:19]=2)[CH:7]=[N:6][CH:5]=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:8]3[CH:7]=[N:6][CH:5]=[C:4]([CH:9]=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 117667397HCID 117667397, compound

Product 1

HCID 86305668HCID 86305668, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-nicotinic acid methyl ester (205 mg, 0.76 mmol) in 60 mL of anhydrous DCM is added benzoyl isocyanate (170 mg, 1.1 mmol) and the solution is heated to reflux for 3 hrs. Then the solvent is removed in vacuo and to the residue is added 60 mL of MeOH. Then K2CO3 (180 mg, 1.3 mmol) is added and the mixture is heated to reflux for 0.5 hr. After cooling down, the organic solvent is evaporated. The residue is taken up in water and washed with DCM. The aqueous layer is separated and purified by neutral preparative HPLC to give 120 mg of the titled product.

Workup

  1. temperaturethe solution is heated
  2. temperatureto reflux for 3 hrs
  3. customThen the solvent is removed in vacuo and to the residue
  4. additionis added 60 mL of MeOH
  5. temperaturethe mixture is heated
  6. temperatureto reflux for 0.5 hr
  7. temperatureAfter cooling down
  8. customthe organic solvent is evaporated
  9. washwashed with DCM
  10. customThe aqueous layer is separated
  11. custompurified by neutral preparative HPLC

Sources & evidence

ORD record
ord-72e8453287dc40888434387954afced2
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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