Sulfuric Acid → 4-(4-Carbamoyl-2-(2,6-difluorophenyl)oxazol-5-ylamino)benzoic acid

HRID 715010

Reaction equation

HRID 715010 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([C:18]2[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=2[F:25])[O:6][C:7]=1[NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)#[N:2].S(=O)(=O)(O)[OH:27]>>[C:1]([C:3]1[N:4]=[C:5]([C:18]2[C:19]([F:25])=[CH:20][CH:21]=[CH:22][C:23]=2[F:24])[O:6][C:7]=1[NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:16][CH:17]=1)(=[O:27])[NH2:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 595874924-(4-Cyano-2-(2,6-difluorophenyl)oxazol-5-ylamino)benzoic acid

Product 1

HCID 595876424-(4-Carbamoyl-2-(2,6-difluorophenyl)oxazol-5-ylamino)benzoic acidYield 57%

Procedure

A solution of 4-(4-cyano-2-(2,6-difluorophenyl)oxazol-5-ylamino)benzoic acid (0.962 g, 2.819 mmol) in concentrated sulfuric acid (5 mL) was stirred at room temperature for 1.5 hours. The reaction mixture was added to ice water and a precipitate formed. The precipitate was isolated by filtration and the remaining aqueous layer extracted with ethyl acetate. The organic layer was combined with the precipitate and reduced in vacuo to yield 4-(4-carbamoyl-2-(2,6-difluorophenyl)oxazol-5-ylamino)benzoic acid (0.580 g, 1.614 mmol, 57%) as a yellow solid. 1H NMR (DMSO) δ 7.35 (2H, t), 7.46 (4H, m), 7.65 (1H, m), 7.87 (2H, d), 9.71 (1H, s), 12.64 (1H, br s). LCMS (2) Rt: 1.37 min; m/z (ES+) 360.

Workup

  1. customa precipitate formed
  2. customThe precipitate was isolated by filtration
  3. extractionthe remaining aqueous layer extracted with ethyl acetate

Sources & evidence

ORD record
ord-6185aae367384661940afbec8d9538fb
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Linked notes

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