Hydrochloric Acid → N-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}benzene-1,2-diamine

HRID 244402노트

반응식

HRID 244402 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH:11]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[N:20]=[CH:19]2)[C:12]([F:15])([F:14])[F:13])([O-])=O.Cl.C(=O)(O)[O-].[Na+]>CO.[Zn]>[F:15][C:12]([F:13])([F:14])[CH:11]([NH:10][C:5]1[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[N:20]=[CH:19]2

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59437215(2-Nitrophenyl)-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}amine

생성물 1

HCID 24960191N-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}benzene-1,2-diamine수율 14%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

실험 절차

To a solution of 100 mg (0.23 mmol) of (2-nitrophenyl)-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}amine in 10 mL of methanol was added 304 mg (4.65 mmol) of zinc powder followed by the addition of 4.65 mL (4.65 mmol) of 1 N aqueous HCl. After 1 hour, the mixture was made basic with saturated aqueous sodium bicarbonate and extracted with three 15 mL portions of ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by prep-TLC using 10-20% EtOAc/hexanes to provide 10 mg (14%) of the title compound as a white solid. MS m/z 401 (MH+).

후처리

  1. extractionextracted with three 15 mL portions of ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

출처 및 근거

ORD 기록
ord-643e4eecb17d4f46ab63ae14627652fd
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658637B2

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