Sodium borohydride → 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-hydroxy-ethylamino)-methyl]-benzamide

HRID 20781Notes

Reaction equation

HRID 20781 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:5]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=2[F:31])=[C:6]([CH:14]=[C:15](/[CH:18]=[N:19]/[CH2:20][CH2:21][OH:22])[C:16]=1[F:17])[C:7]([NH:9][O:10][CH2:11][CH2:12][OH:13])=[O:8]>CO>[F:3][C:4]1[C:5]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=2[F:31])=[C:6]([CH:14]=[C:15]([CH2:18][NH:19][CH2:20][CH2:21][OH:22])[C:16]=1[F:17])[C:7]([NH:9][O:10][CH2:11][CH2:12][OH:13])=[O:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178523984HCID 178523984, compound

Product 1

HCID 593480303,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-hydroxy-ethylamino)-methyl]-benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride was added to a solution of the imine, 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-{[(E)-2-hydroxy-ethylimino]-methyl}-benzamide obtained in Step A in MeOH at 0° C. While being allowed to warm gradually, the mixture was stirred overnight. The solvent was removed under reduced pressure, and the residue was purified with a silica gel column (CH2Cl2:MeOH (4:1 to 2:1)) to give the title compound as a white solid.

Workup

  1. temperatureto warm gradually
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified with a silica gel column (CH2Cl2:MeOH (4:1 to 2:1))

Sources & evidence

ORD record
ord-09151eaca3034e44ab41b36efd620821
Source dataset
uspto-grants-2010_06
Patent number
US07745663B2

Reaction notes

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