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

HRID 1410507Notes

Reaction equation

HRID 1410507 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-03d124979eec4fa0bc04b9bf05565bd6
Source dataset
uspto-grants-2014_12
Patent number
US08921544B2

Reaction notes

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