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Water → (S)-3-(4-bromo-2-fluoro-5-methylphenoxy)-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)pyrrolidin-2-one

HRID 407986
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HRID 407986 반응식
Cl.[Br:2][C:3]1[C:21]([CH3:22])=[CH:20][C:6]([O:7][C@H:8]2[CH2:12][CH2:11][N:10]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:9]2=[O:19])=[C:5]([F:23])[CH:4]=1.C(N(C(C)C)C(C)C)C.Cl[C:34]1[N:39]=[CH:38][C:37]([CH2:40][CH3:41])=[CH:36][N:35]=1.O>CS(C)=O>[Br:2][C:3]1[C:21]([CH3:22])=[CH:20][C:6]([O:7][C@H:8]2[CH2:12][CH2:11][N:10]([CH:13]3[CH2:18][CH2:17][N:16]([C:34]4[N:39]=[CH:38][C:37]([CH2:40][CH3:41])=[CH:36][N:35]=4)[CH2:15][CH2:14]3)[C:9]2=[O:19])=[C:5]([F:23])[CH:4]=1
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HCID 962WaterHCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidineHCID 67469732(S)-3-(4-bromo-2-fluoro-5-methylphenoxy)-1-(piperidin-4-yl)pyrrolidin-2-one hydrochloride

생성물 1

HCID 54671182(S)-3-(4-bromo-2-fluoro-5-methylphenoxy)-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)pyrrolidin-2-one수율 59.9%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
110 °C

실험 절차

(S)-3-(4-bromo-2-fluoro-5-methylphenoxy)-1-(piperidin-4-yl)pyrrolidin-2-one hydrochloride (600 mg, 1.47 mmol) was dissolved in DMSO (10 mL) and N-ethyl-N-isopropylpropan-2-amine (641 μl, 3.68 mmol) and 2-chloro-5-ethylpyrimidine (252 mg, 1.77 mmol) were added and the reaction heated to 110° C. overnight. The reaction was cooled to ambient temperature, poured into water and extracted with EtOAc, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (60% EtOAc in hexanes) to afford (S)-3-(4-bromo-2-fluoro-5-methylphenoxy)-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)pyrrolidin-2-one (420 mg, 0.880 mmol, 59.8% yield) as a tan solid.

후처리

  1. temperatureThe reaction was cooled to ambient temperature
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified over silica gel (60% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-b2684b9c488342a4b9add86e8fda3dc5
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08754226B2

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