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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
ノート
印刷プレビュー

反応式

HRID 407986 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidineHCID 67469732(S)-3-(4-bromo-2-fluoro-5-methylphenoxy)-1-(piperidin-4-yl)pyrrolidin-2-one hydrochloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-b2684b9c488342a4b9add86e8fda3dc5
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08754226B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート