Acetic Anhydride → HCID 59519434, compound

HRID 558215Notes

Reaction equation

HRID 558215 reaction equation
[C:1](OC(=O)C)(=O)[CH3:2].[Cl:8][C:9]1[C:10]([NH:27][NH2:28])=[N:11][CH:12]=[C:13]([C:17]=1[NH:18][C:19]1[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:20]=1[F:26])[C:14]([OH:16])=[O:15].C(N(CC)CC)C.O=P(Cl)(Cl)Cl>C(Cl)Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Cl:8][C:9]1[C:10]2[N:11]([C:1]([CH3:2])=[N:28][N:27]=2)[CH:12]=[C:13]([C:14]([OH:16])=[O:15])[C:17]=1[NH:18][C:19]1[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:20]=1[F:26]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 59519464HCID 59519464, compound

Product 1

HCID 59519434HCID 59519434, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Acetic anhydride (0.95 mmol) is added to a solution of 5-chloro-4-(2-fluoro-4-iodophenylamino)-6-hydrazinylnicotinic acid (0.4 g, 0.95 mmol) and triethylamine (1.9 mmol) in DCM (10 ml) at 0° C. The reaction mixture is warmed to room temperature, stirred for an additional 10 min and POCl3 (0.95 mmol) is added. After stirring overnight at room temperature the mixture is refluxed for 3 days. It was diluted with EtOAc and NaHCO3 and stirred for 20 min. The organic layer is washed with H2O, brine, dried with Na2SO4 and concentrated under reduced pressure. The crude product is purified by column chromatography.

Workup

  1. stirringAfter stirring overnight at room temperature the mixture
  2. temperatureis refluxed for 3 days
  3. stirringstirred for 20 min
  4. washThe organic layer is washed with H2O, brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-ca5be185fd214fbabfa5534352cf0f47
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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