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

HRID 561633

반응식

HRID 561633 반응식
FC(F)(F)C(O)=O.[CH3:8][S:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][CH:17]=[CH:16]2.[CH:20]1([C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(O)[CH3:24])[CH2:22][CH2:21]1>ClCCl>[CH:20]1([C:23]([C:16]2[C:15]3[C:19](=[C:11]([CH2:10][S:9][CH3:8])[CH:12]=[CH:13][CH:14]=3)[NH:18][CH:17]=2)([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)[CH3:24])[CH2:22][CH2:21]1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 98258alpha-Cyclopropyl-alpha,4-dimethylbenzenemethanolHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

생성물 1

HCID 583922803-[1-Cyclopropyl-1-(4-methylphenyl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

0.23 ml (3.00 mmol) of trifluoroacetic acid was added to 885 mg (4.99 mmol) of the compound from Example 8A and 440 mg (2.50 mmol) of the compound from Example 137A in 44 ml of dichloromethane, and the mixture was stirred at RT overnight. The reaction mixture was concentrated in a rotary evaporator. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 87.4 mg (10% of theory) of the title compound as mixture of diastereomers.

후처리

  1. concentrationThe reaction mixture was concentrated in a rotary evaporator
  2. customThe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

출처 및 근거

ORD 기록
ord-4da1d5476b2e4fe384010306eb100e3c
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

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