Dichloromethane → 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-5-[(E)-[2-(methylamino)-2-oxoethoxy]iminomethyl]benzamide

HRID 2038613Notes

Reaction equation

HRID 2038613 reaction equation
[NH2:1][O:2][CH2:3][C:4]([NH:6][CH3:7])=[O:5].C(Cl)Cl.[F:11][C:12]1[C:13]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=2[F:36])=[C:14]([CH:22]=[C:23]([CH:26]=O)[C:24]=1[F:25])[C:15]([NH:17][O:18][CH2:19][CH2:20][OH:21])=[O:16]>C1COCC1>[F:11][C:12]1[C:13]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=2[F:36])=[C:14]([CH:22]=[C:23](/[CH:26]=[N:1]/[O:2][CH2:3][C:4](=[O:5])[NH:6][CH3:7])[C:24]=1[F:25])[C:15]([NH:17][O:18][CH2:19][CH2:20][OH:21])=[O:16]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 231323432-(Aminooxy)-n-methylacetamideHCID 231323883,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-5-formyl-N-(2-hydroxy-ethoxy)-benzamide

Product 1

HCID 231323223,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-5-[(E)-[2-(methylamino)-2-oxoethoxy]iminomethyl]benzamideYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminooxy-N-methyl-acetamide (1.71 g, 16.4 mmol) obtained in Step B in a mixed solvent of methylene chloride (50 ml) and THF (25 ml) was added 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-5-formyl-N-(2-hydroxy-ethoxy)-benzamide (3.94 g, 8.20 mmol) obtained in Step F of Example 1 at room temperature, and the mixture was stirred for 15 hours. The reaction mixture was concentrated under reduced pressure, and methylene chloride (40 ml) was added to the resultant residue to precipitate a solid, which was filtered and washed with methylene chloride. The resultant solid was dried under reduced pressure to give (E)-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[methylcarbamoylmethoxyimino-methyl]-benzamide (3.57 g, 77%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and methylene chloride (40 ml)
  2. additionwas added to the resultant residue
  3. customto precipitate a solid, which
  4. filtrationwas filtered
  5. washwashed with methylene chloride
  6. customThe resultant solid was dried under reduced pressure

Sources & evidence

ORD record
ord-f6a11591077349308cd1cb94cd4050d1
Source dataset
uspto-grants-2013_11
Patent number
US08575391B2

Reaction notes

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