Acetyl chloride → Acetamide, N-(4-amino-5-cyano-6-ethoxy-2-pyridinyl)-

HRID 1364512ノート

反応式

HRID 1364512 の反応式
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([NH2:13])[CH:3]=1.[C:14](Cl)(=[O:16])[CH3:15]>N1C=CC=CC=1.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([NH:13][C:14](=[O:16])[CH3:15])[CH:3]=1

参加物

5

反応物 2

HCID 6367Acetyl chlorideHCID 131498684,6-Diamino-2-ethoxypyridine-3-carbonitrile

生成物 1

HCID 11715520Acetamide, N-(4-amino-5-cyano-6-ethoxy-2-pyridinyl)-収率 50.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1049Pyridine溶媒

実験手順

To 50 mg (0.28 mmol) of 4,6-diamino-2-ethoxy-nicotinonitrile dissolved in 1 mL of pyridine was added 60 μL (0.84 mmol) of acetyl chloride. The mixture was stirred at ambient temperature for 2 hours then diluted with 7 mL of water. The precipitate was filtered and washed with 5 mL of water. The supernatant was extracted with ethyl acetate (3×5 mL), then the combined ethyl acetate layers were back extracted with brine (1×5 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to a solid. This was combined with the precipitated product, dissolved in methanol/ethyl acetate, and concentrated. Most of the remaining pyridine was removed by coevaporation with toluene under reduced pressure. The product was purified via silica gel chromatography, eluting with 50% ethyl acetate/hexanes to provide 31 mg (50%) of a white solid. 1H NMR (300 MHz, d6-DMSO) δ 10.73 (s, 1H), 7.17 (s, 1H), 6.88 (s, 2H), 4.32 (q, 2H, J=7.1 Hz), 2.07 (s, 3H), 1.29 (t, 3H, J=7.1 Hz); MS (ESI) m/e=221 (M+H)+, m/e=219 (M−H)−.

後処理

  1. filtrationThe precipitate was filtered
  2. washwashed with 5 mL of water
  3. extractionThe supernatant was extracted with ethyl acetate (3×5 mL)
  4. extractionthe combined ethyl acetate layers were back extracted with brine (1×5 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure to a solid
  8. dissolutiondissolved in methanol/ethyl acetate
  9. concentrationconcentrated
  10. customMost of the remaining pyridine was removed by coevaporation with toluene under reduced pressure
  11. customThe product was purified via silica gel chromatography
  12. washeluting with 50% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-16b4dd17213f44859f18f1ddcee52a09
出典データセット
uspto-grants-2011_02
特許番号
US07888374B2

反応ノート

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