Dichloroacetic Acid → HCID 11534476, compound

HRID 20743Notes

Reaction equation

HRID 20743 reaction equation
[CH2:1]([NH:3][C:4]([CH2:6][CH2:7][O:8]/[N:9]=[CH:10]/[C:11]1[C:12]([F:34])=[C:13]([F:33])[C:14]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=2[F:32])=[C:15]([CH:23]=1)[C:16]([NH:18][O:19][CH2:20][CH2:21][OH:22])=[O:17])=[O:5])[CH3:2].ClC(Cl)C(O)=O>ClCCl>[CH2:1]([NH:3][C:4]([CH2:6][CH2:7][O:8][NH:9][CH2:10][C:11]1[C:12]([F:34])=[C:13]([F:33])[C:14]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=2[F:32])=[C:15]([CH:23]=1)[C:16]([NH:18][O:19][CH2:20][CH2:21][OH:22])=[O:17])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6597Dichloroacetic AcidHCID 59348012HCID 59348012, compound

Product 1

HCID 11534476HCID 11534476, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (E)-5-[(2-ethylcarbamoyl-ethoxyimino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (40 mg, 0.067 mmol) obtained in Step B was added dichloromethane (2 ml). The mixture was stirred at room temperature, and borane-pyridine complex (40 μl) and dichloroacetic acid (40 μl) were added thereto. After stirring for 1 hour, the reaction mixture was poured into purified water, and the resultant mixture was extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 5-[(2-ethylcarbamoyl-ethoxyamino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (C-18, 29 mg, 75% yield).

Workup

  1. stirringAfter stirring for 1 hour
  2. additionthe reaction mixture was poured
  3. custominto purified water
  4. extractionthe resultant mixture was extracted with dichloromethane
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-34fe0e435bf54f26b4e568ecdeeccb0d
Source dataset
uspto-grants-2010_06
Patent number
US07745663B2

Reaction notes

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