Trifluoroacetic acid → 3-[1-Cyclopropyl-1-(4-fluorophenyl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561578

반응식

HRID 561578 반응식
[CH:1]1([C:4]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)(O)[CH3:5])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[CH3:21][S:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:32]=1[NH:31][CH:30]=[CH:29]2>ClCCl>[CH:1]1([C:4]([C:29]2[C:28]3[C:32](=[C:24]([CH2:23][S:22][CH3:21])[CH:25]=[CH:26][CH:27]=3)[NH:31][CH:30]=2)([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[CH3:5])[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 981041-Cyclopropyl-1-(4-fluorophenyl)ethanolHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

생성물 1

HCID 583921063-[1-Cyclopropyl-1-(4-fluorophenyl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

559 mg (3.10 mmol) of the compound from Example 77A and 0.26 ml (3.39 mmol) of trifluoroacetic acid were added to 500 mg (2.82 mmol) of the compound from Example 8A in 12 ml of dichloromethane. The reaction mixture was stirred at RT for 30 min and then diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. Purification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 361 mg (38% of theory) of the title compound.

후처리

  1. washwashed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient)

출처 및 근거

ORD 기록
ord-0be2306708914b3e9eb50432c2e77ae8
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

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