m-Chloroperbenzoic acid → N-cyclopentyl-4-[2-isobutyl-7-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine

HRID 859973ノート

反応式

HRID 859973 の反応式
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([CH2:24][CH:25]([CH3:27])[CH3:26])=[N:15][N:16]4[C:21]([S:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-:29].[Na+].ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([CH2:24][CH:25]([CH3:27])[CH3:26])=[N:15][N:16]4[C:21]([S:22]([CH3:23])=[O:29])=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 10339828N-cyclopentyl-4-[2-isobutyl-7-(methylthio)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine

生成物 1

HCID 10453435N-cyclopentyl-4-[2-isobutyl-7-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine収率 99%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a cold (0° C.) solution of N-cyclopentyl-4-[2-isobutyl-7-(methylthio)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine (700 mg, 1.83 mmol) in dichloromethane (30 mL) was added sodium bicarbonate solid (500 mg), and m-chloroperbenzoic acid (451 mg, ˜70% pure, 1.83 mmol). The mixture was stirred at 0° C. for 20 minutes and then quenched by the addition of saturated aqueous sodium thiosulfate and saturated aqueous sodium bicarbonate. The biphasic mixture was allowed to warm to room temperature and stirred vigorously for 15 minutes. The layers were separated and the organic layer washed with brine. The aqueous layer was extracted with dichloromethane and the combined organics were dried over sodium sulfate. Filtration and concentration in vacuo provided N-cyclopentyl-4-[2-isobutyl-7-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine (720 mg, 99%) as a yellow solid. 1H NMR (CDCl3) δ 8.38–8.29 (m, 2H), 7.51–7.44 (m, 2H), 6.77 (d, 1H), 5.24 (m, 1H), 4.38 (m, 1H), 3.13 (s, 3H), 3.08–2.91 (m, 2H), 2.25–2.05 (m, 3H), 1.82–1.54 (m, 6H), 0.98 (m, 6H); MS m/z 398 (M+1).

後処理

  1. customquenched by the addition of saturated aqueous sodium thiosulfate and saturated aqueous sodium bicarbonate
  2. temperatureto warm to room temperature
  3. stirringstirred vigorously for 15 minutes
  4. customThe layers were separated
  5. washthe organic layer washed with brine
  6. extractionThe aqueous layer was extracted with dichloromethane
  7. dry with materialthe combined organics were dried over sodium sulfate
  8. filtrationFiltration and concentration in vacuo

出典と根拠

ORDレコード
ord-83b42719fcf7437dad1db953d08e92d7
出典データセット
uspto-grants-2006_12
特許番号
US07153863B2

反応ノート

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