Methanol → 3-(ethylsulfinyl)-2-phenyl-N-((S)-1-phenylpropyl)quinoline-4-carboxamide

HRID 2425513

반응식

HRID 2425513 반응식
[CH2:1]([S:3][C:4]1[C:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:6][C:7]2[C:12]([C:13]=1[C:14]([NH:16][C@H:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:18][CH3:19])=[O:15])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2].C[OH:33]>O.CCOC(C)=O>[CH2:1]([S:3]([C:4]1[C:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:6][C:7]2[C:12]([C:13]=1[C:14]([NH:16][C@H:17]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:18][CH3:19])=[O:15])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:33])[CH3:2]

참가 물질

5

반응물 2

HCID 887MethanolHCID 593234873-(ethylthio)-2-phenyl-N-[(1S)-1-phenylpropyl]quinolin-4-carboxamide

생성물 1

HCID 160653913-(ethylsulfinyl)-2-phenyl-N-((S)-1-phenylpropyl)quinoline-4-carboxamide수율 28.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a solution of 3-(ethylthio)-2-phenyl-N-[(1S)-1-phenylpropyl]quinolin-4-carboxamide (5) (300 mg, 0.70 mmol) in MeOH (25 mL) was added a solution of NaIO4 (300 mg, 1.4 mmol) in water (15 mL) while it was cooled to 0° C. The cooling bath was removed, and reaction allowed stir for 12 h. LCMS indicated no reaction take place. Added another 2 eq of NaIO4 and the reaction mixture was heated to reflux for 8 h. It was then diluted with EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10-35% EtOAc/CH2Cl2) to give the desired product (two diastereomers) as a solid (88 mg, 28.4%). 1H NMR (300 MHz, CDCl3) δ 0.97 (t, 3H), 1.21 (t, 3H), 2.01 (m, 2H), 2.71 (m, 2H), 5.21 (q, 1H), 7.21 (d, 2H), 7.34 (d, 2H), 7.39 (m, 2H), 7.78 (m, 2H), 7.84 (m, 2H), 8.00 (m, 1H), 8.11 (m, 2H), 8.14 (m, 1H), 8.16 (m, 1H). MS APCI, m/z=443 (M+1). LCMS: 2.15 min.

후처리

  1. customThe cooling bath was removed
  2. customreaction
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for 8 h
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (10-35% EtOAc/CH2Cl2)

출처 및 근거

ORD 기록
ord-14d13d05a57d4386b5efca1edf3211be
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964733B2

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