Hydrochloric Acid → 5-[(E)-2-aminoethoxyiminomethyl]-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)benzamide

HRID 2038626노트

반응식

HRID 2038626 반응식
C(OC(=O)[NH:7][CH2:8][CH2:9][O:10]/[N:11]=[CH:12]/[C:13]1[CH:18]=[C:17]([C:19](=[O:25])[NH:20][O:21][CH2:22][CH2:23][OH:24])[C:16]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])=[C:15]([F:35])[C:14]=1[F:36])(C)(C)C.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:7][CH2:8][CH2:9][O:10]/[N:11]=[CH:12]/[C:13]1[C:14]([F:36])=[C:15]([F:35])[C:16]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])=[C:17]([CH:18]=1)[C:19]([NH:20][O:21][CH2:22][CH2:23][OH:24])=[O:25]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 11445081HCID 11445081, 화합물

생성물 1

HCID 113072055-[(E)-2-aminoethoxyiminomethyl]-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)benzamide수율 37%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of {2-[2,3-difluoro-4-(2-fluoro-4-iodo-phenylamino)-5-(2-hydroxy-ethoxycarbamoyl)-benzylideneaminooxy]-ethyl}-carbamic acid tert-butyl ester (55 mg, 0.31 mmol) prepared in Step B in ethyl acetate (5 ml) was added 1 N HCl solution in ethyl acetate (1 ml), and the mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the reaction mixture was neutralized with saturated solution of sodium bicarbonate (50 ml), and extracted with ethyl acetate (3×100 ml). The extract was washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated under reduced pressure, and after washing with diethyl ether (10 ml), the residue was recrystallized from methanol to give (E)-5-[(2-amino-ethoxyimino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (17.31 mg, 37% yield) as a pale yellow solid.

후처리

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe extract was washed with saturated brine
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. washafter washing with diethyl ether (10 ml)
  8. customthe residue was recrystallized from methanol

출처 및 근거

ORD 기록
ord-27617004e4fc4f469f81a0f58d64ec34
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575391B2

반응 노트

불러오는 중…