Trifluoroacetic acid → HCID 11689297, compound

HRID 2387352Notes

Reaction equation

HRID 2387352 reaction equation
C([O:5][NH:6][C:7]([C:9]1[C:14]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[F:23])=[C:13]([F:24])[C:12](=[O:25])[N:11]([CH3:26])[CH:10]=1)=[O:8])(C)(C)C.C(O)(C(F)(F)F)=O>>[OH:5][NH:6][C:7]([C:9]1[C:14]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[F:23])=[C:13]([F:24])[C:12](=[O:25])[N:11]([CH3:26])[CH:10]=1)=[O:8]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 57636820HCID 57636820, compound2×

Product 1

HCID 11689297HCID 11689297, compoundYield 33%

Procedure

4-(4-Bromo-2-fluorophenylamino)-5-fluoro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid hydroxyamide was prepared from 4-(4-bromo-2-fluorophenylamino)-5-fluoro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid tert-butoxy-amide by TFA mediated deprotection. 4-(4-Bromo-2-fluorophenylamino)-5-fluoro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid tert-butoxy-amide (35 mg, 0.081 mmol) was treated with TFA (0.63 mL). After 4 days stirring, the reaction mixture was concentrated under reduced pressure. Purification by flash column chromatography (10% MeOH in methylene chloride) followed by saturated NaHCO3 solution wash of an ethyl acetate solution of the product gave clean desired product (10 mg, 33%); MS APCI (+) m/z 356, 358 (M—OH, Br pattern) detected; 1H NMR (400 mHz, CD3OD) δ 7.84 (s, 1H), 7.35 (dd, 1H), 7.28 (d, 1H), 7.01 (td, 1H), 3.57 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customPurification by flash column chromatography (10% MeOH in methylene chloride)
  3. washwash of an ethyl acetate solution of the product

Sources & evidence

ORD record
ord-efb35cce7fab4d23a9f0b0a9cfebd9ba
Source dataset
uspto-grants-2012_09
Patent number
US08268852B2

Reaction notes

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