Potassium Carbonate → HCID 117667365, compound

HRID 712644Notes

Reaction equation

HRID 712644 reaction equation
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([C:11]2[CH:12]=[C:13]([C:17]([OH:20])([CH3:19])[CH3:18])[CH:14]=[N:15][CH:16]=2)[CH:2]=1.[C:21]([N:29]=C=O)(=[O:28])C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[OH:20][C:17]([C:13]1[CH:12]=[C:11]([C:3]2[CH:4]=[C:5]3[C:10](=[N:1][CH:2]=2)[N:9]([C:21]([NH2:29])=[O:28])[CH2:8][CH2:7][CH2:6]3)[CH:16]=[N:15][CH:14]=1)([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 117667614HCID 117667614, compound

Product 1

HCID 117667365HCID 117667365, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

2-[5-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-yl]-propan-2-ol (33 mg, 0.12 mmol) and benzoyl isocyanate (40 mg, 0.25 mmol) are mixed in 1.0 mL of DCM and the mixture is heated at 50° C. for 16 hrs. Then the solvent is removed and the residue is dissolved in 1.0 mL of EtOH. K2CO3 (29 mg, 0.21 mmol) is added and the mixture is heated at 80° C. for 2 hrs, cooled down to room temperature for 16 hrs and heated at 80° C. again for another 3 hrs. Then the solvent is removed and the residue is partitioned between water (15 mL) and EtOAc (25 mL). The aqueous layer is separated and extracted with EtOAc (2×30 mL). The organic layers are combined and concentrated to give the crude product. The crude is purified by flash column chromatography to give 12 mg of the titled product.

Workup

  1. customThen the solvent is removed
  2. dissolutionthe residue is dissolved in 1.0 mL of EtOH
  3. temperaturethe mixture is heated at 80° C. for 2 hrs
  4. temperaturecooled down to room temperature for 16 hrs
  5. temperatureheated at 80° C. again for another 3 hrs
  6. customThen the solvent is removed
  7. customthe residue is partitioned between water (15 mL) and EtOAc (25 mL)
  8. customThe aqueous layer is separated
  9. extractionextracted with EtOAc (2×30 mL)
  10. concentrationconcentrated
  11. customto give the crude product
  12. customThe crude is purified by flash column chromatography

Sources & evidence

ORD record
ord-70c4758f60af40288d3a4e9331128fe1
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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