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Triacetoxyperiodinane → 1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]-3-[3-(1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]pyrrolidin-2-one

HRID 522322
ノート
印刷プレビュー

反応式

HRID 522322 の反応式
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH:15]2[CH2:19][CH2:18][N:17]([C:20]3[CH:21]=[N:22][N:23]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:24]=3[CH:25]([CH3:27])[CH3:26])[C:16]2=[O:35])[N:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CS(C)=O>[F:34][C:31]1[CH:32]=[CH:33][C:28]([N:23]2[C:24]([CH:25]([CH3:27])[CH3:26])=[C:20]([N:17]3[CH2:18][CH2:19][CH:15]([N:8]4[C:9]5=[N:10][CH:11]=[CH:12][CH:13]=[C:14]5[C:6]([C:2]5[NH:3][CH:4]=[CH:5][N:1]=5)=[N:7]4)[C:16]3=[O:35])[CH:21]=[N:22]2)=[CH:29][CH:30]=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

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 867230363-[3-(4,5-dihydro-1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one

生成物 1

HCID 1362158841-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]-3-[3-(1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]pyrrolidin-2-one収率 82.7%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3-[3-(4,5-dihydro-1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (0.085 g, 0.18 mmol) and Dess-Martin periodinane (0.153 g, 0.36 mmol) in DMSO (2.5 mL) was stirred at 80° C. for 1 hr. It was then cooled to room temperature, quenched with sat. aq. NaHCO3 (50 mL), and extracted with EtOAc (50 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash chromatography (SiO2, 0˜7% MeOH/EtOAc gradient elution) to give the title compound (0.070 g, 82%). 1H NMR (400 MHz, CDCl3) δ 10.42 (s, 1H, br), 8.74 (dd, J=8.4, 1.6 Hz, 1H), 8.54 (dd, J=4.8, 1.6 Hz, 1H), 7.64 (s, 1H), 7.40 (dd, J=6.8, 4.6 Hz, 2H), 7.23 (m, 1H), 7.18 (dd, J=8.6 Hz, 2H), 6.94 (s, 1H, br), 5.94 (dd, J=9.2, 9.2 Hz, 1H), 3.94 (m, 3H), 3.07 (heptet, J=6.8, 1H), 2.75-2.95 (m, 2H), 1.33 (d, J=7.6 Hz, 3H), 1.28 (d, J=7.2 Hz, 3H); MS: (ES) m/z calculated for C25H23FN8O [M+H]+471.2. found 471.2.

後処理

  1. temperatureIt was then cooled to room temperature
  2. customquenched with sat. aq. NaHCO3 (50 mL)
  3. extractionextracted with EtOAc (50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (SiO2, 0˜7% MeOH/EtOAc gradient elution)

出典と根拠

ORDレコード
ord-b94c8743ff3c45699035575a9a8361e2
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09328116B2

反応ノート

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