Ethyl Acetate → HCID 178448113, compound

HRID 2252851Notes

Reaction equation

HRID 2252851 reaction equation
C[Si](I)(C)C.[CH:6]([C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16]2[N:25]=[CH:24][C:23]([CH2:26][C:27]3[CH:28]=[N:29][C:30]([O:33]C)=[CH:31][CH:32]=3)=[C:22]3[C:17]=2[CH:18]=[CH:19][CH:20]=[N:21]3)[CH2:11][CH2:10]1)([CH3:8])[CH3:7].CCOC(C)=O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH:6]([C@H:9]1[CH2:10][CH2:11][C@H:12]([NH:15][C:16]2[N:25]=[CH:24][C:23]([CH2:26][C:27]3[CH:28]=[N:29][C:30]([OH:33])=[CH:31][CH:32]=3)=[C:22]3[C:17]=2[CH:18]=[CH:19][CH:20]=[N:21]3)[CH2:13][CH2:14]1)([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 178489835HCID 178489835, compound

Product 1

HCID 178448113HCID 178448113, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under a N2 atmosphere, 142 μl (1.02 mmol) of trimethylsilyl iodide are added to 400 mg (1.02 mmol) of trans 5-(4-isopropyl-cyclohexylamino)-8-[(6-methoxy-pyridin-3-yl)-methyl]-[1,6]naphthyridine in 7 ml of chloroform, and stirring is effected for 12 h at 70° C. The mixture is cooled, EtOAc and diluted NaHCO3 are added, stirring is effected until everything has dissolved, the organic phase is separated and washed with water and brine. The aqueous phases are extracted twice more with EtOAc. Drying (Na2SO4), concentrating by evaporation, column chromatography (SiO2, EtOAc/EtOH 5:1) and stirring with DIPE yield trans 5-(4-isopropyl-cyclohexylamino)-8-[(6-hydroxy-pyridin-3-yl)-methyl]-[1,6]naphthyridine; m.p. 232-235° C.; FAB-MS: (M+H)+=377.

Workup

  1. temperatureThe mixture is cooled
  2. stirringstirring
  3. dissolutionhas dissolved
  4. customthe organic phase is separated
  5. washwashed with water and brine
  6. extractionThe aqueous phases are extracted twice more with EtOAc
  7. dry with materialDrying (Na2SO4)
  8. concentrationconcentrating by evaporation, column chromatography (SiO2, EtOAc/EtOH 5:1)
  9. stirringstirring with DIPE

Sources & evidence

ORD record
ord-ffca01d27e06466296391a345d32c1ff
Source dataset
uspto-grants-2008_01
Patent number
US07323474B2

Reaction notes

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