Potassium Carbonate → HCID 86305713, compound

HRID 712606Notes

Reaction equation

HRID 712606 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]1[CH:12]=[C:13]([C:17]2[CH:18]=[C:19]3[C:24](=[N:25][CH:26]=2)[NH:23][CH2:22][CH2:21][CH2:20]3)[CH:14]=[N:15][CH:16]=1.[C:27]([N:35]=C=O)(=[O:34])C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]1[CH:12]=[C:13]([C:17]2[CH:18]=[C:19]3[C:24](=[N:25][CH:26]=2)[N:23]([C:27]([NH2:35])=[O:34])[CH2:22][CH2:21][CH2:20]3)[CH:14]=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 117667584HCID 117667584, compound

Product 1

HCID 86305713HCID 86305713, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-[5-(1-methyl-1H-indol-2-yl)-pyridin-3-yl]-1,2,3,4-tetrahydro-[1,8]naphthyridine (110 mg; 0.32 mmol) in anhydrous DCM (5.0 mL) is added benzoyl isocyanate (71 mg; 0.48 mmol). The mixture is heated to reflux for 3 hrs. The solvent is removed and the residue is dissolved in EtOH (5.0 ml). K2CO3 (76 mg; 0.55 mmol) is added and the mixture is heated to reflux for 1 hr. Then the solvent is removed and the residue is purified by preparative HPLC to give 74 mg of the titled product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 3 hrs
  3. customThe solvent is removed
  4. dissolutionthe residue is dissolved in EtOH (5.0 ml)
  5. temperaturethe mixture is heated
  6. temperatureto reflux for 1 hr
  7. customThen the solvent is removed
  8. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-50c83410bf464fa28baf5153c67987a3
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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