Hydrochloric Acid → 4-(4-Aminofuro[3,2-c]pyridin-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile

HRID 1910667ノート

反応式

HRID 1910667 の反応式
[C:1]([C:3]1[CH:8]([C:9]2[O:17][C:16]3[CH:15]=[CH:14][N:13]=[C:12]([NH:18]C(=O)C4C=CC=CC=4)[C:11]=3[CH:10]=2)[C:7]([C:27]#[N:28])=[C:6]([CH3:29])[NH:5][C:4]=1[CH3:30])#[N:2].Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[NH2:18][C:12]1[C:11]2[CH:10]=[C:9]([CH:8]3[C:7]([C:27]#[N:28])=[C:6]([CH3:29])[NH:5][C:4]([CH3:30])=[C:3]3[C:1]#[N:2])[O:17][C:16]=2[CH:15]=[CH:14][N:13]=1

参加物

5

反応物 3

HCID 313Hydrochloric Acid2 回HCID 10340Sodium CarbonateHCID 52938807N-[2-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)furo[3,2-c]pyridin-4-yl]benzamide

生成物 1

HCID 529205034-(4-Aminofuro[3,2-c]pyridin-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile収率 18%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

A solution of 43 mg (0.11 mmol) N-[2-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)furo[3,2-c]pyridin-4-yl]benzamide (Example 4) in acetic acid (3 ml) was treated with 0.2 ml hydrochloric acid (37%) and stirred for 24 h at 100° C. Then, further 0.2 ml hydrochloric acid (37%) were added, and stirring was continued for 48 h at 100° C. Upon cooling, saturated aq. sodium carbonate solution was added until a neutral pH was reached. The mixture was extracted with ethyl acetate, and the organic layer was washed with brine and water, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was purified by preparative thin layer chromatography (silica, eluent dichloromethane/methanol 10:1 v/v) to afford the title compound (5.6 mg, 18% of th.) as a white solid.

後処理

  1. stirringstirring
  2. waitwas continued for 48 h at 100° C
  3. temperatureUpon cooling
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with brine and water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by preparative thin layer chromatography (silica, eluent dichloromethane/methanol 10:1 v/v)

出典と根拠

ORDレコード
ord-671a3c3159754a598f2e9892b1b64c49
出典データセット
uspto-grants-2013_12
特許番号
US08604028B2

反応ノート

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