Acetamide → HCID 57863417, compound

HRID 2075291Notes

Reaction equation

HRID 2075291 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:16]2[C:11]([CH:12]=[C:13]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:14]=[N:15]2)=[C:10](I)[N:9]=1)=[O:7].[C:35]([NH2:38])(=[O:37])[CH3:36].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(OCC)(=O)C.O1CCOCC1>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:16]2[C:11]([CH:12]=[C:13]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:14]=[N:15]2)=[C:10]([NH:38][C:35](=[O:37])[CH3:36])[N:9]=1)=[O:7]

Participants

9

Reactant 4

HCID 178AcetamideHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 59696213HCID 59696213, compound

Product 1

HCID 57863417HCID 57863417, compoundYield 80.9%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To Compound 10 (571 mg, 1 mmol) and acetic acid amide (89 mg, 1.5 mmol) was added and solved dioxane (12 ml), and were added cesium carbonate (48.8 mg, 1.5 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxancene (88 mg, 0.152 mmol), and palladium acetate (24 mg, 0.107 mmol) under stirring at room temperature in nitrogen gas flow, and then the solution was stirred for 5 hours under heating in an oil bath at 70° C. The mixture was added with ethyl acetate, water and ammonium chloride aqueous solution for extraction, washed with sodium chloride aqueous solution, dried over sodium sulfate and the subjected to distillation. The obtained residue was subjected to silica gel chromatography and recrystallized from acetone-diisopropyl ether, to give 5-acetylamino-8-benzyloxy-3-(4-fluorobenzyl)[1,6]naphthyridine-7-carboxylic acid (2-methoxyethyl) amide 12 (245 mg, 80.9%) as colorless crystals.

Workup

  1. stirringthe solution was stirred for 5 hours
  2. temperatureunder heating in an oil bath at 70° C
  3. washwashed with sodium chloride aqueous solution
  4. dry with materialdried over sodium sulfate
  5. distillationthe subjected to distillation
  6. customrecrystallized from acetone-diisopropyl ether

Sources & evidence

ORD record
ord-72f5c5d8a92c4161887ce3bff78e09a7
Source dataset
uspto-grants-2011_04
Patent number
US07919623B2

Reaction notes

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