Acetone → Pyridine, 3-(4-(isopropylamino)pyrazol-1-yl)-

HRID 1484722ノート

反応式

HRID 1484722 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([NH2:12])[CH:9]=[N:8]2)[CH:2]=1.[CH3:13][C:14]([CH3:16])=O.FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(OC(C)C)(=O)C>[CH:14]([NH:12][C:10]1[CH:9]=[N:8][N:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:11]=1)([CH3:16])[CH3:13]

参加物

6

反応物 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 206682Pyridine, 3-(4-aminopyrazol-1-yl)-HCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 206683Pyridine, 3-(4-(isopropylamino)pyrazol-1-yl)-

試薬・触媒・溶媒 1

HCID 7915Isopropyl Acetate溶媒

実験手順

1-pyridin-3-yl-1H-pyrazol-4-ylamine (0.6 g, 3.7 mmol) was dissolved in isopropyl acetate (8.5 ml). To the mixture, acetone (0.261 g, 4.5 mmol), trifluoroacetic acid (0.855 g, 7.5 mmol) and sodium triacetoxyborohydride (0.945 g, 4.5 mmol) were added. The reaction was stirred under nitrogen at room temperature for 4.5 hours and then quenched with 10% sodium hydroxide solution until the pH reached˜9. The layers were separated, and the aqueous phase was extracted with ethyl acetate. The organic extracts were combined, dried over sodium sulfate and concentrated to dryness. The crude material was purified by silica gel chromatography (gradient elution of 5% methanol/dichloromethane) to give the title compound as an off white solid (0.35 g, 46%): mp 105-107° C.; 1H NMR (300 MHz, CDCl3) δ 8.82 (d, J=2.2 Hz, 1H), 8.63 (dd, J=4.8, 1.5 Hz, 1H), 8.13 (d, J=1.8 Hz, 1H), 8.03 (d, J=2.7 Hz, 1H), 7.94-7.77 (m, 1H), 7.38 (dt, J=15.2, 7.6 Hz, 1H), 6.99 (t, 1H), 3.72 (m, 1H), 1.30 (t, J=10.0 Hz, 6H). ESIMS 214 m/z (M+1).

後処理

  1. customquenched with 10% sodium hydroxide solution until the pH reached˜9
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe crude material was purified by silica gel chromatography (gradient elution of 5% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-866ad14aecd443bb9229f82453a79fb4
出典データセット
uspto-grants-2016_08
特許番号
US09422278B2

反応ノート

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