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

HRID 389778

반응식

HRID 389778 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-1b9d4584c6e94078810b7ffa39a0a9e0
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08378095B2

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