Potassium Carbonate → HCID 117667177, compound
Reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH2:7][C:8]2[CH:9]=[C:10]([C:14]3[CH:15]=[C:16]4[C:21](=[N:22][CH:23]=3)[NH:20][CH2:19][CH2:18][CH2:17]4)[CH:11]=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[C:26]([N:34]=C=O)(=[O:33])C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[F:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH2:7][C:8]2[CH:9]=[C:10]([C:14]3[CH:15]=[C:16]4[C:21](=[N:22][CH:23]=3)[N:20]([C:26]([NH2:34])=[O:33])[CH2:19][CH2:18][CH2:17]4)[CH:11]=[N:12][CH:13]=2)=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
6-[5-(4-Fluoro-phenoxymethyl)-pyridin-3-yl]-1,2,3,4-tetrahydro-[1,8]naphthyridine (32 mg, 0.096 mmol) and benzoyl isocyanate (24 mg, 0.14 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 (23 mg, 0.16 mmol) is added and the mixture is heated at 80° C. for 45 min. Then the solvent is removed and the residue is partitioned between water (35 mL) and EtOAc (75 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. Purification by flash column chromatography affords 26 mg of the titled product.
Workup
- customThen the solvent is removed
- dissolutionthe residue is dissolved in 1.0 mL of EtOH
- temperaturethe mixture is heated at 80° C. for 45 min
- customThen the solvent is removed
- customthe residue is partitioned between water (35 mL) and EtOAc (75 mL)
- customThe aqueous layer is separated
- extractionextracted with EtOAc (2×30 mL)
- concentrationconcentrated
- customto give the crude product
- customPurification by flash column chromatography
Sources & evidence
- ORD record
- ord-0405592b07744df4843ef76e9215d00c
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181272B2
Reaction notes
Loading…